Electronic device

ABSTRACT

The present application relates to an electronic device comprising a xanthene or thioxanthene compound of a particular formula. The electronic device is preferably an organic electroluminescent device (OLED). The application further relates to particular xanthene or thioxanthene compounds as such, and to the use thereof in the abovementioned devices, and to processes for preparation thereof.

The present application relates to an electronic device comprising axanthene or thioxanthene compound of a formula defined further down. Theelectronic device is preferably an organic electroluminescent device(OLED). The application further relates to particular xanthene orthioxanthene compounds as such, to the use thereof in the abovementioneddevices, and to processes for preparation thereof.

Electronic devices in the context of this application are understood tomean organic electronic devices, i.e. devices which contain organicsemiconductor materials as functional materials. More particularly,these are understood to mean OLEDs. The term OLEDs is understood to meanelectronic devices which have one or more layers comprising organiccompounds and emit light on application of electrical voltage. Theconstruction and general principle of function of OLEDs are known tothose skilled in the art.

In electronic devices, especially OLEDs, there is great interest inimproving the performance data, especially lifetime, efficiency andoperating voltage. In these aspects, it has not yet been possible tofind any entirely satisfactory solution.

A great influence on the performance data of electronic devices ispossessed by layers having a hole-transporting function. These layersinclude hole-injecting layers, hole transport layers and electronblocker layers. For use in these layers, new materials havinghole-transporting properties are still being sought.

In addition, there is a need for new device constructions, and for newcombinations of functional materials in different layers of the OLEDs.What are of significance here are especially the layers having ahole-transporting function, the composition thereof and the sequencethereof, in order to improve the performance data of OLEDs.

The prior art, for example in published specifications WO 2014/072017and CN 103666454, describes xanthene and thioxanthene compounds thatbear an arylamino group as OLED functional materials.

Compared to the OLED constructions comprising the compounds mentionedthat are described therein, however, there is still a need forimprovement with regard to the performance data of the OLEDs, especiallyoperating voltage, lifetime and efficiency.

In addition, there is still a need for improvement with regard to thespecific compounds disclosed therein.

In the context of the present invention, it has been found that OLEDscontaining particular xanthene or thioxanthene compounds in a layeradjoining the anode, or comprising these compounds in a layer having atleast two further layers between this layer and the emitting layerclosest to the anode, have excellent performance data.

It has additionally been found that particular novel xanthene orthioxanthene compounds have excellent performance data.

The present invention therefore provides an electronic devicecomprising, in this sequence, an anode, a hole-transporting layer, anemitting layer and a cathode, wherein said hole-transporting layercomprises a compound of a formula (I)

where:

-   A is an arylamino group optionally substituted by one or more R¹    radicals, or a carbazole-containing group optionally substituted by    one or more R¹ radicals;-   E is a single bond;-   X is O or S;-   Z is the same or different at each instance and is CR² or N or C,    where a Z group is C in the specific case when an A or E group is    bonded to the Z group in question;-   R¹ is the same or different at each instance and is selected from H,    D, F, C(═O)R³, CN, Si(R³)₃, N(R³)₂, P(═O)(R³)₂, OR³, S(═O)R³,    S(═O)₂R³, straight-chain alkyl or alkoxy groups having 1 to 20    carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to    20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon    atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and    heteroaromatic ring systems having 5 to 40 aromatic ring atoms;    where two or more R¹ radicals may be joined to one another and may    form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups    mentioned and the aromatic ring systems and heteroaromatic ring    systems mentioned may each be substituted by one or more R³    radicals; and where one or more CH₂ groups in the alkyl, alkoxy,    alkenyl and alkynyl groups mentioned may be replaced    -   by —R³C═CR³—, —C≡C—, Si(R³)₂, C═O, C═NR³, —C(═O)O—, C(═O)NR³—,        NR³, P(═O)(R³), —O—, —S—, SO or SO₂;-   R² is the same or different at each instance and is selected from H,    D, F, C(═O)R³, CN, Si(R³)₃, N(R³)₂, P(═O)(R³)₂, OR³, S(═O)R³,    S(═O)₂R³, straight-chain alkyl or alkoxy groups having 1 to 20    carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to    20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon    atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and    heteroaromatic ring systems having 5 to 40 aromatic ring atoms;    where two or more R² radicals may be joined to one another and may    form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups    mentioned and the aromatic ring systems and heteroaromatic ring    systems mentioned may each be substituted by one or more R³    radicals; and where one or more CH₂ groups in the alkyl, alkoxy,    alkenyl and alkynyl groups mentioned may be replaced    -   by —R³C═CR³—, —C≡C—, Si(R³)₂, C═O, C═NR³, —C(═O)O—, C(═O)NR³—,        NR³, P(═O)(R³), —O—, —S—, SO or SO₂;-   R³ is the same or different at each instance and is selected from H,    D, F, C(═O)R⁴, CN, Si(R⁴)₃, N(R⁴)₂, P(═O)(R⁴)₂, OR⁴, S(═O)R⁴,    S(═O)₂R⁴, straight-chain alkyl or alkoxy groups having 1 to 20    carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to    20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon    atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and    heteroaromatic ring systems having 5 to 40 aromatic ring atoms;    where two or more R³ radicals may be joined to one another and may    form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups    mentioned and the aromatic ring systems and heteroaromatic ring    systems mentioned may each be substituted by one or more R⁴    radicals; and where one or more CH₂ groups in the alkyl, alkoxy,    alkenyl and alkynyl groups mentioned may be replaced    -   by —R⁴C═CR⁴—, —C≡C—, Si(R⁴)₂, C═O, C═NR⁴, —C(═O)O—, C(═O)NR⁴—,        NR⁴, P(═O)(R⁴), —O—, —S—, SO or SO₂;-   R⁴ is the same or different at each instance and is selected from H,    D, F, CN, alkyl or alkoxy groups having 1 to 20 carbon atoms,    alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring    systems having 6 to 40 aromatic ring atoms and heteroaromatic ring    systems having 5 to 40 aromatic ring atoms; where two or more R⁴    radicals may be joined to one another and may form a ring; and where    the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems    and heteroaromatic ring systems mentioned may be substituted by F or    CN;-   is 0 or 1;-   n is the same or different at each instance and is 0 or 1, where the    sum total of all the indices n is 1, 2, 3 or 4;

where at least one condition selected from conditions a) and b) is met:

-   -   a) the hole-transporting layer directly adjoins the anode;    -   b) there are at least two further layers arranged between the        hole-transporting layer and the emitting layer, and there are no        further emitting layers arranged between the emitting layer and        the anode.

The application further provides xanthene and thioxanthene compounds ofa particular formula (S) as such, which are defined and describedfurther down.

An arylamino group as A group is understood to mean a group comprisingat least one unit in which at least one aryl group or heteroaryl groupis bonded to a trivalent nitrogen atom. The further structure of thegroup and whether it comprises further units and, if so, which units areimmaterial to the definition.

A carbazole-containing group as A group is also understood to meangroups containing derivatives of carbazole, for example carbazole groupshaving fused-on benzene rings, or azacarbazole compounds. The furtherstructure of the group and whether it comprises further units and, ifso, which units are immaterial to the definition.

An aryl group in the context of this invention contains 6 to 40 aromaticring atoms of which none is a heteroatom. An aryl group in the contextof this invention is understood to mean either a simple aromatic cycle,i.e. benzene, or a fused aromatic polycycle, for example naphthalene,phenanthrene or anthracene. A fused aromatic polycycle in the context ofthe present application consists of two or more simple aromatic cyclesfused to one another. Fusion between cycles is understood here to meanthat the cycles share at least one edge with one another.

A heteroaryl group in the context of this invention contains 5 to 40aromatic ring atoms of which at least one is a heteroatom. Theheteroatoms of the heteroaryl group are preferably selected from N, Oand S. A heteroaryl group in the context of this invention is understoodto mean either a simple heteroaromatic cycle, for example pyridine,pyrimidine or thiophene, or a fused heteroaromatic polycycle, forexample quinoline or carbazole. A fused heteroaromatic polycycle in thecontext of the present application consists of two or more simpleheteroaromatic cycles fused to one another. Fusion between cycles isunderstood here to mean that the cycles share at least one edge with oneanother.

An aryl or heteroaryl group, each of which may be substituted by theabovementioned radicals and which may be joined to the aromatic orheteroaromatic system via any desired positions, is especiallyunderstood to mean groups derived from benzene, naphthalene, anthracene,phenanthrene, pyrene, dihydropyrene, chrysene, perylene, triphenylene,fluoranthene, benzanthracene, benzophenanthrene, tetracene, pentacene,benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene,benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole,isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine,phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline,benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole,imidazole, benzimidazole, naphthimidazole, phenanthrimidazole,pyridimidazole, pyrazinimidazole, quinoxalinimidazole, oxazole,benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole,1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine,pyrimidine, benzopyrimidine, quinoxaline, pyrazine, phenazine,naphthyridine, azacarbazole, benzocarboline, phenanthroline,1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole,1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole,1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine,1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine,1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine andbenzothiadiazole.

An aromatic ring system in the context of this invention contains 6 to40 carbon atoms in the ring system and does not include any heteroatomsas aromatic ring atoms. An aromatic ring system in the context of thisinvention therefore does not contain any heteroaryl groups. An aromaticring system in the context of this invention shall be understood to meana system which does not necessarily contain only aryl groups but inwhich it is also possible for a plurality of aryl groups to be bonded bya single bond or by a non-aromatic unit, for example one or moreoptionally substituted C, Si, N, O or S atoms. In this case, thenonaromatic unit comprises preferably less than 10% of the atoms otherthan H, based on the total number of atoms other than H in the system.For example, systems such as 9,9′-spirobifluorene, 9,9′-diarylfluorene,triarylamine, diaryl ethers and stilbene are also to be regarded asaromatic ring systems in the context of this invention, and likewisesystems in which two or more aryl groups are joined, for example, by alinear or cyclic alkyl, alkenyl or alkynyl group or by a silyl group. Inaddition, systems in which two or more aryl groups are joined to oneanother via single bonds are also regarded as aromatic ring systems inthe context of this invention, for example systems such as biphenyl andterphenyl.

A heteroaromatic ring system in the context of this invention contains 5to 40 aromatic ring atoms, at least one of which is a heteroatom. Theheteroatoms of the heteroaromatic ring system are preferably selectedfrom N, O and/or S. A heteroaromatic ring system corresponds to theabovementioned definition of an aromatic ring system, but has at leastone heteroatom as one of the aromatic ring atoms. In this way, itdiffers from an aromatic ring system in the sense of the definition ofthe present application, which, according to this definition, cannotcontain any heteroatom as aromatic ring atom.

An aromatic ring system having 6 to 40 aromatic ring atoms or aheteroaromatic ring system having 5 to 40 aromatic ring atoms isespecially understood to mean groups derived from the groups mentionedabove under aryl groups and heteroaryl groups, and from biphenyl,terphenyl, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene,dihydropyrene, tetrahydropyrene, indenofluorene, truxene, isotruxene,spirotruxene, spiroisotruxene, indenocarbazole, or from combinations ofthese groups.

In the context of the present invention, a straight-chain alkyl grouphaving 1 to 20 carbon atoms and a branched or cyclic alkyl group having3 to 20 carbon atoms and an alkenyl or alkynyl group having 2 to 40carbon atoms in which individual hydrogen atoms or CH₂ groups may alsobe substituted by the groups mentioned above in the definition of theradicals are preferably understood to mean the methyl, ethyl, n-propyl,i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl,s-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl,n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl,trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl,propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl,heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl,butynyl, pentynyl, hexynyl or octynyl radicals.

An alkoxy or thioalkyl group having 1 to 20 carbon atoms in whichindividual hydrogen atoms or CH₂ groups may also be replaced by thegroups mentioned above in the definition of the radicals is preferablyunderstood to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy,i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy,2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy,n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy,2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio,i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio,n-pentylthio, s-pentylthio, n-hexytthio, cyclohexylthio, n-heptylthio,cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexytthio,trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio,ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio,hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio,octenyfthio, cyclooctenylthio, ethynylthio, propynylthio, butynylthio,pentynylthio, hexynylthio, heptynylthio or octynylthio.

The wording that two or more radicals together may form a ring, in thecontext of the present application, shall be understood to mean, interalia, that the two radicals are joined to one another by a chemicalbond. In addition, however, the abovementioned wording shall also beunderstood to mean that, if one of the two radicals is hydrogen, thesecond radical binds to the position to which the hydrogen atom wasbonded, forming a ring.

In the compound of the formula (I), X is preferably O.

In addition, i is preferably 1.

In addition, the sum total of the indices n in formula (I) is preferably1 or 2, more preferably 1.

In addition, preferably not more than 2 Z groups per ring are N. Inaddition, preferably not more than 4 Z groups per compound of theformula (I), most preferably not more than 2 Z groups per compound ofthe formula (I), are Z.

More preferably, Z is CR², where, in the case that an A or E group isbonded to the Z group in question, this Z group is C.

Preferably, R¹ is the same or different at each instance and is selectedfrom H, D, F, CN, Si(R³)₃, straight-chain alkyl or alkoxy groups having1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ringatoms and heteroaromatic ring systems having 5 to 40 aromatic ringatoms, where the alkyl and alkoxy groups mentioned, the aromatic ringsystems mentioned and the heteroaromatic ring systems mentioned may eachbe substituted by one or more R³ radicals; and where one or more CH₂groups in the alkyl or alkoxy groups mentioned may be replaced

by —C≡C—, —R³C═CR³—, Si(R³)₂, C═O, C═NR³, —NR³—, —O—, —S—, —C(═O)O—

or —C(═O)NR³—.

More preferably, R¹ is the same or different at each instance and isselected from H, F, CN, straight-chain alkyl groups having 1 to 20carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbonatoms, aromatic ring systems having 6 to 40 aromatic ring atoms andheteroaromatic ring systems having 5 to 40 aromatic ring atoms; wheresaid alkyl groups, said aromatic ring systems and said heteroaromaticring systems may each be substituted by one or more R³ radicals.

Preferably, R² is the same or different at each instance and is selectedfrom H, D, F, CN, Si(R³)₃, straight-chain alkyl or alkoxy groups having1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ringatoms and heteroaromatic ring systems having 5 to 40 aromatic ringatoms, where the alkyl and alkoxy groups mentioned, the aromatic ringsystems mentioned and the heteroaromatic ring systems mentioned may eachbe substituted by one or more R³ radicals; and where one or more CH₂groups in the alkyl or alkoxy groups mentioned may be replaced

by —C≡C—, —R³C═CR³—, Si(R³)₂, C═O, C═NR³, —NR³—, —O—, —S—, —C(═O)O—

or —C(═O)NR³—.

More preferably, R² is the same or different at each instance and isselected from H, F, CN, straight-chain alkyl groups having 1 to 20carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbonatoms, aromatic ring systems having 6 to 40 aromatic ring atoms andheteroaromatic ring systems having 5 to 40 aromatic ring atoms; wheresaid alkyl groups, said aromatic ring systems and said heteroaromaticring systems may each be substituted by one or more R³ radicals.

Most preferably, R² is H.

Preferably, R³ is the same or different at each instance and is selectedfrom H, D, F, CN, Si(R⁴)₃, straight-chain alkyl or alkoxy groups having1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ringatoms and heteroaromatic ring systems having 5 to 40 aromatic ringatoms, where the alkyl and alkoxy groups mentioned, the aromatic ringsystems mentioned and the heteroaromatic ring systems mentioned may eachbe substituted by one or more R⁴ radicals; and where one or more CH₂groups in the alkyl or alkoxy groups mentioned may be replaced

by —C≡C—, —R⁴C═CR⁴—, Si(R⁴)₂, C═O, C═NR⁴, —NR⁴—, —O—, —S—, C(═O)O— or—C(═O)NR⁴—.

More preferably, R³ is the same or different at each instance and isselected from H, F, CN, straight-chain alkyl groups having 1 to 20carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbonatoms, aromatic ring systems having 6 to 40 aromatic ring atoms andheteroaromatic ring systems having 5 to 40 aromatic ring atoms; wheresaid alkyl groups, said aromatic ring systems and said heteroaromaticring systems may each be substituted by one or more R⁴ radicals.

Preferably, the A group is an arylamino group which may be substitutedby one or more R¹ radicals.

The arylamino group as A group preferably corresponds to a formula (A)

where:

-   L¹ is the same or different at each instance and is C═O, Si(R¹)₂,    PR¹, P(═O)(R¹), O, S, SO, SO₂, an alkylene group having 1 to 20    carbon atoms or an alkenylene or alkynylene group having 2 to 20    carbon atoms, where one or more CH₂ groups in the groups mentioned    may be replaced by C═O, C═NR¹, C═O—O, C═O—NR¹, Si(R¹)₂, NR¹,    P(═O)(R¹), O, S, SO or SO₂ and where one or more hydrogen atoms in    the abovementioned groups may be replaced by D, F or CN, or an    aromatic or heteroaromatic ring system which has 6 to 24 aromatic    ring atoms and may be substituted by one or more R¹ radicals;-   Ar¹ is the same or different at each instance and is an aromatic or    heteroaromatic ring system which has 6 to 30 aromatic ring atoms and    may be substituted by one or more R¹ radicals;-   Y is selected from a single bond, BR¹, C(R¹)₂, C(R¹)₂—C(R¹)₂,    Si(R¹)₂, Si(R¹)₂—Si(R¹)₂, C═O, C═NR¹, C═C(R¹)₂, C(═O)N(R¹), O, S,    S═O, SO₂ and NR¹;-   k is 0, 1, 2 or 3;-   m is 0 or 1;

where the A group is bonded to the rest of the compound of the formula(I) via the bond marked with *.

Preferably, in formula (A), L¹ is the same or different at each instanceand is Si(R¹)₂, O, S, an alkylene group having 1 to 10 carbon atoms oran alkenylene or alkynylene group having 2 to 10 carbon atoms, where oneor more CH₂ groups in the groups mentioned may be replaced by Si(R¹)₂, Oor S and where one or more hydrogen atoms in the abovementioned groupsmay be replaced by D, F or CN, or an aromatic or heteroaromatic ringsystem which has 6 to 24 aromatic ring atoms and may be substituted byone or more R¹ radicals.

More preferably, L¹ is the same or different at each instance and is anaromatic or heteroaromatic ring system which has 6 to 18 aromatic ringatoms and may be substituted by one or more R¹ radicals. Mostpreferably, L¹ is the same or different at each instance and is phenyl,biphenyl, naphthyl, terphenyl, fluorenyl, spirobifluorene,indenofluorenyl, carbazole, dibenzofuran or dibenzothiophene, each ofwhich may be substituted by one or more R¹ radicals.

Particularly preferred L¹ groups are the following groups:

where the dotted bonds indicate the bonds from L¹ to the rest of thecompound, and where the groups may each be substituted by R¹ radicals atthe positions shown as unsubstituted, and where the groups arepreferably not substituted by R¹ radicals at the positions shown asunsubstituted.

In addition, k in formula (A) is preferably 0 or 1, more preferably 0.

In addition, m in formula (A) is preferably 0, meaning that the two Ar¹groups are not bonded to one another.

In addition, Ar¹ in formula (A) is the same or different at eachinstance and is an aromatic or heteroaromatic ring system which has 6 to24 aromatic ring atoms and may be substituted by one or more R¹radicals. Among these, very particular preference is given to phenyl,biphenyl, naphthyl, terphenyl, fluorenyl, spirobifluorene,indenofluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl, whichmay be substituted by one or more R¹ radicals.

Preferred Ar¹ groups are depicted in the following table:

Ar¹-1

Ar¹-3

Ar¹-3

Ar¹-4

Ar¹-5

Ar¹-6

Ar¹-7

Ar¹-8

Ar¹-9

Ar¹-10

Ar¹-11

Ar¹-12

Ar¹-13

Ar¹-14

Ar¹-15

Ar¹-16

Ar¹-17

Ar¹-18

Ar¹-19

Ar¹-20

Ar¹-21

Ar¹-22

Ar¹-23

Ar¹-24

Ar¹-25

Ar¹-26

Ar¹-27

Ar¹-28

Ar¹-29

Ar¹-30

Ar¹-31

Ar¹-32

Ar¹-33

Ar¹-34

Ar¹-35

Ar¹-36

Ar¹-37

Ar¹-38

Ar¹-39

Ar¹-40

Ar¹-41

Ar¹-42

Ar¹-43

Ar¹-44

Ar¹-45

Ar¹-46

Ar¹-47

Ar¹-48

Ar¹-49

Ar¹-50

Ar¹-51

Ar¹-52

Ar¹-53

Ar¹-54

Ar¹-55

Ar¹-56

Ar¹-57

Ar¹-58

Ar¹-59

Ar¹-60

Ar¹-61

Ar¹-62

Ar¹-63

Ar¹-64

Ar¹-65

Ar¹-66

Ar¹-67

Ar¹-68

Ar¹-69

Ar¹-70

Ar¹-71

Ar¹-72

Ar¹-73

Ar¹-74

Ar¹-75

Ar¹-76

Ar¹-77

Ar¹-78

Ar¹-79

Ar¹-80

Ar¹-81

Ar¹-82

Ar¹-83

Ar¹-84

Ar¹-85

Ar¹-86

Ar¹-87

Ar¹-88

Ar¹-89

Ar¹-90

Ar¹-91

Ar¹-92

Ar¹-93

Ar¹-94

Ar¹-95

Ar¹-96

Ar¹-94

Ar¹-95

Ar¹-96

Ar¹-97

Ar¹-98

Ar¹-99

Ar¹-100

Ar¹-101

Ar¹-102

Ar¹-103

Ar¹-104

Ar¹-105

Ar¹-106

Ar¹-107

Ar¹-108

Ar¹-109

Ar¹-110

Ar¹-111

Ar¹-112

Ar¹-113

Ar¹-114

Ar¹-115

Ar¹-116

Ar¹-117

Ar¹-118

Ar¹-119

Ar¹-120

Ar¹-121

Ar¹-122

Ar¹-123

Ar¹-124

Ar¹-125

Ar¹-126

Ar¹-127

Ar¹-128

Ar¹-129

Ar¹-130

Ar¹-131

Ar¹-132

Ar¹-133

Ar¹-134

Ar¹-135

Ar¹-136

Ar¹-137

Ar¹-138

Ar¹-139

Ar¹-140

Ar¹-141

Ar¹-142

Ar¹-143

Ar¹-144

Ar¹-145

Ar¹-146

Ar¹-147

Ar¹-148

Ar¹-149

Ar¹-150

Ar¹-151

Ar¹-152

Ar¹-153

Ar¹-154

Ar¹-155

Ar¹-156

Ar¹-157

Ar¹-158

Ar¹-159

Ar¹-160

Ar¹-161

Ar¹-162

Ar¹-163

Ar¹-164

Ar¹-165

Ar¹-166

Ar¹-167

Ar¹-168

Ar¹-169

Ar¹-170

Ar¹-171

Ar¹-172

Ar¹-173

Ar¹-174

Ar¹-175

Ar¹-176

Ar¹-177

Ar¹-178

Ar¹-179

Ar¹-180

Ar¹-181

Ar¹-182

Ar¹-183

Ar¹-184

Ar¹-185

Ar¹-186

Ar¹-187

Ar¹-188

Ar¹-189

Ar¹-190

Ar¹-191

Ar¹-192

Ar¹-193

Ar¹-194

Ar¹-195

Ar¹-196

Ar¹-197

Ar¹-198

Ar¹-199

Ar¹-200

Ar¹-201

Ar¹-202

Ar¹-203

Ar¹-204

Ar¹-205

Ar¹-206

Ar¹-207

Ar¹-208

Ar¹-209

Ar¹-210

Ar¹-211

Ar¹-212

Ar¹-213

Ar¹-214

Ar¹-215

Ar¹-216

Ar¹-217

Ar¹-218

Ar¹-219

Ar¹-220

Ar¹-221

Ar¹-222

Ar¹-223

Ar¹-224

Ar¹-225

Ar¹-226

Ar¹-227

Ar¹-228

Ar¹-229

Ar¹-230

Ar¹-231

Ar¹-232

Ar¹-233

Ar¹-234

Ar¹-235

Ar¹-236

Ar¹-237

Ar¹-238

Ar¹-239

Ar¹-240

Ar¹-241

Ar¹-242

Ar¹-243

Ar¹-244

Ar¹-245

Ar¹-246

The groups shown above may each be substituted by R¹ radicals at theirpositions shown as unsubstituted.

Among the Ar¹ groups mentioned, particular preference is given to theAr¹-1, Ar¹-2, Ar¹-3, Ar¹4, Ar¹-5, Ar¹-6, Ar¹-15, Ar¹-16, Ar¹-46, Ar¹-47,Ar¹-48, Ar¹-55, Ar¹-59, Ar¹-60, Ar¹-61, Ar¹-62, Ar¹-63, Ar¹-64, Ar¹-65,Ar¹-66, Ar¹-67, Ar¹-70, Ar¹-74, Ar¹-78, Ar¹-82, Ar¹-89, Ar¹-92, Ar¹-100,Ar¹-101, Ar¹-102, Ar¹-104, Ar¹-107, Ar¹-110, Ar¹-113, Ar¹-127, Ar¹-132,Ar¹-133, Ar¹-134, Ar¹-135, Ar¹-136, Ar¹-137, Ar¹-143, Ar¹-145, Ar¹-147,Ar¹-163, Ar¹-164, Ar¹-165, Ar¹-166, Ar¹-167, Ar¹-168, Ar¹-188, Ar¹-189,Ar¹-200, Ar¹-201, Ar¹-202, Ar¹-203 and Ar¹-232 groups. Among theabovementioned Ar¹ groups, very particular preference is given to theAr¹-1, Ar¹-74, Ar¹-132, Ar¹-134, Ar¹-136, Ar¹-137, Ar¹-165, Ar¹-200 andAr¹-201 groups.

In addition, the Y group in formula (A) is preferably selected from asingle bond, C(R¹)₂, O, S and NR¹. More preferably, Y is a single bond.

When the A group is a carbazole-containing group, it is preferably acarbazole group as such and in the narrower sense, or an indenocarbazolegroup as such and in the narrower sense. The carbazole group may bebonded to the rest of the compound via its nitrogen atom, or via one ofits benzene rings.

Particularly preferred A groups correspond to the following formulae:

where the groups may be substituted at all unoccupied positions by oneor more R¹ radicals as defined above. It is preferable that R¹ radicalshere are defined as per their preferred embodiments. Preferably, thecompounds are unsubstituted at their unoccupied positions.

A preferred embodiment of the compound of the formula (I) corresponds tothe following formula (I-1):

where the variables that occur are as defined above. Preferably, thevariables that occur correspond to their abovementioned preferredembodiments.

Particularly preferred embodiments of the compounds of the formula (I)correspond to the following formulae:

where the variables that occur are as defined above, and where thecompounds may each be substituted on the benzene rings at the positionsshown as unsubstituted by R² radicals. Preferably, the compounds areeach unsubstituted on the benzene rings at the positions shown asunsubstituted.

Most preferably, the compound corresponds to one of the formulae (I-1-1)to (I-1-8), most preferably to one of the formulae (I-1-1) to (I-1-3).For compounds of this kind, particularly good performance data have beenfound in the case of use in the device of the invention.

Preferably, in the above formulae, L₁ is selected from aromatic andheteroaromatic ring systems which have 6 to 24 aromatic ring atoms andmay be substituted by one or more R¹ radicals.

Preferably, in the above formulae, k is 0 or 1.

Particular preference is given to the combination of the formulae(I-1-1) to (I-1-20) and (I-2-1) to (I-2-7) with the preferredembodiments of Ar¹.

Particularly preferred definitions of the compounds of the formula (I)are shown in the following table, where the variables are as definedabove and there are preferably no further substituents other than thosementioned:

Base L¹ skeleton k = 0 Ar¹ Ar¹ 1 I-1-2-O k = 0 Ar¹-1  Ar¹-1  2 s.o. s.o.s.o. Ar¹-74  3 s.o. s.o. s.o. Ar¹-132 4 s.o. s.o. s.o. Ar¹-134 5 s.o.s.o. s.o. Ar¹-136 6 s.o. s.o. s.o. Ar¹-137 7 s.o. s.o. s.o. Ar¹-165 8s.o. s.o. s.o. Ar¹-200 9 s.o. s.o. s.o. Ar¹-201 10 s.o. s.o. Ar¹-74 Ar¹-74  11 s.o. s.o. s.o. Ar¹-132 12 s.o. s.o. s.o. Ar¹-134 13 s.o. s.o.s.o. Ar¹-136 14 s.o. s.o. s.o. Ar¹-137 15 s.o. s.o. s.o. Ar¹-136 16 s.o.s.o. s.o. Ar¹-200 17 s.o. s.o. s.o. Ar¹-201 18 s.o. s.o. Ar¹-132 Ar¹-13219 s.o. s.o. s.o. Ar¹-134 20 s.o. s.o. s.o. Ar¹-136 21 s.o. s.o. s.o.Ar¹-137 22 s.o. s.o. s.o. Ar¹-165 23 s.o. s.o. s.o. Ar¹-200 24 s.o. s.o.s.o. Ar¹-201 25 s.o. s.o. Ar¹-134 Ar¹-134 26 s.o. s.o. s.o. Ar¹-136 27s.o. s.o. s.o. Ar¹-137 28 s.o. s.o. s.o. Ar¹-165 29 s.o. s.o. s.o.Ar¹-200 30 s.o. s.o. s.o. Ar¹-201 31 s.o. s.o. Ar¹-136 Ar¹-136 32 s.o.s.o. s.o. Ar¹-137 33 s.o. s.o. s.o. Ar¹-165 34 s.o. s.o. s.o. Ar¹-200 35s.o. s.o. s.o. Ar¹-201 36 s.o. s.o. Ar¹-137 Ar¹-137 37 s.o. s.o. s.o.Ar¹-165 38 s.o. s.o. s.o. Ar¹-200 39 s.o. s.o. s.o. Ar¹-201 40 s.o. s.o.Ar¹-165 Ar¹-165 41 s.o. s.o. s.o. Ar¹-200 42 s.o. s.o. s.o. Ar¹-201 43s.o. s.o. Ar¹-200 Ar¹-200 44 s.o. s.o. s.o. Ar¹-201 45 s.o. s.o. Ar¹-201Ar¹-201 46 s.o. Ar¹-1  Ar¹-1  Ar¹-1  47 s.o. s.o. s.o. Ar¹-74  48 s.o.s.o. s.o. Ar¹-132 49 s.o. s.o. s.o. Ar¹-134 50 s.o. s.o. s.o. Ar¹-136 51s.o. s.o. s.o. Ar¹-137 52 s.o. s.o. s.o. Ar¹-165 53 s.o. s.o. s.o.Ar¹-200 54 s.o. s.o. s.o. Ar¹-201 55 s.o. s.o. Ar¹-74  Ar¹-74  56 s.o.s.o. s.o. Ar¹-132 57 s.o. s.o. s.o. Ar¹-134 58 s.o. s.o. s.o. Ar¹-136 59s.o. s.o. s.o. Ar¹-137 60 s.o. s.o. s.o. Ar¹-165 61 s.o. s.o. s.o.Ar¹-200 62 s.o. s.o. s.o. Ar¹-201 63 s.o. s.o. Ar¹-132 Ar¹-132 64 s.o.s.o. s.o. Ar¹-134 65 s.o. s.o. s.o. Ar¹-136 66 s.o. s.o. s.o. Ar¹-137 67s.o. s.o. s.o. Ar¹-165 68 s.o. s.o. s.o. Ar¹-200 69 s.o. s.o. s.o.Ar¹-201 70 s.o. s.o. Ar¹-134 Ar¹-134 71 s.o. s.o. s.o. Ar¹-136 72 s.o.s.o. s.o. Ar¹-137 73 s.o. s.o. s.o. Ar¹-165 74 s.o. s.o. s.o. Ar¹-200 75s.o. s.o. s.o. Ar¹-201 76 s.o. s.o. Ar¹-136 Ar¹-136 77 s.o. s.o. s.o.Ar¹-137 78 s.o. s.o. s.o. Ar¹-165 79 s.o. s.o. s.o. Ar¹-200 80 s.o. s.o.s.o. Ar¹-201 81 s.o. s.o. Ar¹-137 Ar¹-137 82 s.o. s.o. s.o. Ar¹-165 83s.o. s.o. s.o. Ar¹-200 84 s.o. s.o. s.o. Ar¹-201 85 s.o. s.o. Ar¹-165Ar¹-165 86 s.o. s.o. s.o. Ar¹-200 87 s.o. s.o. s.o. Ar¹-201 88 s.o. s.o.Ar¹-200 Ar¹-200 89 s.o. s.o. s.o. Ar¹-201 90 s.o. s.o. Ar¹-201 Ar¹-20191 s.o. Ar¹-2  Ar¹-1  Ar¹-1  92 s.o. s.o. s.o. Ar¹-74  93 s.o. s.o. s.o.Ar¹-132 94 s.o. s.o. s.o. Ar¹-134 95 s.o. s.o. s.o. Ar¹-136 96 s.o. s.o.s.o. Ar¹-137 97 s.o. s.o. s.o. Ar¹-165 98 s.o. s.o. s.o. Ar¹-200 99 s.o.s.o. s.o. Ar¹-201 100 s.o. s.o. Ar¹-74  Ar¹-74  101 s.o. s.o. s.o.Ar¹-132 102 s.o. s.o. s.o. Ar¹-134 103 s.o. s.o. s.o. Ar¹-136 104 s.o.s.o. s.o. Ar¹-137 105 s.o. s.o. s.o. Ar¹-165 106 s.o. s.o. s.o. Ar¹-200107 s.o. s.o. s.o. Ar¹-201 108 s.o. s.o. Ar¹-132 Ar¹-132 109 s.o. s.o.s.o. Ar¹-134 110 s.o. s.o. s.o. Ar¹-136 111 s.o. s.o. s.o. Ar¹-137 112s.o. s.o. s.o. Ar¹-165 113 s.o. s.o. s.o. Ar¹-200 114 s.o. s.o. s.o.Ar¹-201 115 s.o. s.o. Ar¹-134 Ar¹-134 116 s.o. s.o. s.o. Ar¹-136 117s.o. s.o. s.o. Ar¹-137 118 s.o. s.o. s.o. Ar¹-165 119 s.o. s.o. s.o.Ar¹-200 120 s.o. s.o. s.o. Ar¹-201 121 s.o. s.o. Ar¹-136 Ar¹-136 122s.o. s.o. s.o. Ar¹-137 123 s.o. s.o. s.o. Ar¹-165 124 s.o. s.o. s.o.Ar¹-200 125 s.o. s.o. s.o. Ar¹-201 126 s.o. s.o. Ar¹-137 Ar¹-137 127s.o. s.o. s.o. Ar¹-165 128 s.o. s.o. s.o. Ar¹-200 129 s.o. s.o. s.o.Ar¹-201 130 s.o. s.o. Ar¹-165 Ar¹-165 131 s.o. s.o. s.o. Ar¹-200 132s.o. s.o. s.o. Ar¹-201 133 s.o. s.o. Ar¹-200 Ar¹-200 134 s.o. s.o. s.o.Ar¹-201 135 s.o. s.o. Ar¹-201 Ar¹-201 136 s.o. Ar¹-3  Ar¹-1  Ar¹-1  137s.o. s.o. s.o. Ar¹-74  138 s.o. s.o. s.o. Ar¹-132 139 s.o. s.o. s.o.Ar¹-134 140 s.o. s.o. s.o. Ar¹-136 141 s.o. s.o. s.o. Ar¹-137 142 s.o.s.o. s.o. Ar¹-165 143 s.o. s.o. s.o. Ar¹-200 144 s.o. s.o. s.o. Ar¹-201145 s.o. s.o. s.o. Ar¹-74  146 s.o. s.o. s.o. Ar¹-132 147 s.o. s.o. s.o.Ar¹-134 148 s.o. s.o. s.o. Ar¹-136 149 s.o. s.o. s.o. Ar¹-137 150 s.o.s.o. s.o. Ar¹-165 151 s.o. s.o. s.o. Ar¹-200 152 s.o. s.o. s.o. Ar¹-201153 s.o. s.o. Ar¹-132 Ar¹-132 154 s.o. s.o. s.o. Ar¹-134 155 s.o. s.o.s.o. Ar¹-136 156 s.o. s.o. s.o. Ar¹-137 157 s.o. s.o. s.o. Ar¹-165 158s.o. s.o. s.o. Ar¹-200 159 s.o. s.o. s.o. Ar¹-201 160 s.o. s.o. Ar¹-134Ar¹-134 161 s.o. s.o. s.o. Ar¹-136 162 s.o. s.o. s.o. Ar¹-137 163 s.o.s.o. s.o. Ar¹-165 164 s.o. s.o. s.o. Ar¹-200 165 s.o. s.o. s.o. Ar¹-201166 s.o. s.o. Ar¹-136 Ar¹-136 167 s.o. s.o. s.o. Ar¹-137 168 s.o. s.o.s.o. Ar¹-165 169 s.o. s.o. s.o. Ar¹-200 170 s.o. s.o. s.o. Ar¹-201 171s.o. s.o. Ar¹-137 Ar¹-137 172 s.o. s.o. s.o. Ar¹-165 173 s.o. s.o. s.o.Ar¹-200 174 s.o. s.o. s.o. Ar¹-201 175 s.o. s.o. Ar¹-165 Ar¹-165 176s.o. s.o. s.o. Ar¹-200 177 s.o. s.o. s.o. Ar¹-201 178 s.o. s.o. Ar¹-200Ar¹-200 179 s.o. s.o. s.o. Ar¹-201 180 s.o. s.o. Ar¹-201 Ar¹-201 181I-1-4-O k = 0 Ar¹-1  Ar¹-1  182 s.o. s.o. s.o. Ar¹-74  183 s.o. s.o.s.o. Ar¹-132 184 s.o. s.o. s.o. Ar¹-134 185 s.o. s.o. s.o. Ar¹-136 186s.o. s.o. s.o. Ar¹-137 187 s.o. s.o. s.o. Ar¹-165 188 s.o. s.o. s.o.Ar¹-200 189 s.o. s.o. s.o. Ar¹-201 190 s.o. s.o. Ar¹-74 Ar¹-74  191 s.o.s.o. s.o. Ar¹-132 192 s.o. s.o. s.o. Ar¹-134 193 s.o. s.o. s.o. Ar¹-136194 s.o. s.o. s.o. Ar¹-137 195 s.o. s.o. s.o. Ar¹-165 196 s.o. s.o. s.o.Ar¹-200 197 s.o. s.o. s.o. Ar¹-201 198 s.o. s.o. Ar¹-132 Ar¹-132 199s.o. s.o. s.o. Ar¹-134 200 s.o. s.o. s.o. Ar¹-136 201 s.o. s.o. s.o.Ar¹-137 202 s.o. s.o. s.o. Ar¹-165 203 s.o. s.o. s.o. Ar¹-200 204 s.o.s.o. s.o. Ar¹-201 205 s.o. s.o. Ar¹-134 Ar¹-134 206 s.o. s.o. s.o.Ar¹-136 207 s.o. s.o. s.o. Ar¹-137 208 s.o. s.o. s.o. Ar¹-165 209 s.o.s.o. s.o. Ar¹-200 210 s.o. s.o. s.o. Ar¹-201 211 s.o. s.o. Ar¹-136Ar¹-136 212 s.o. s.o. s.o. Ar¹-137 213 s.o. s.o. s.o. Ar¹-165 214 s.o.s.o. s.o. Ar¹-200 215 s.o. s.o. s.o. Ar¹-201 216 s.o. s.o. Ar¹-137Ar¹-137 217 s.o. s.o. s.o. Ar¹-165 218 s.o. s.o. s.o. Ar¹-200 219 s.o.s.o. s.o. Ar¹-201 220 s.o. s.o. Ar¹-165 Ar¹-165 221 s.o. s.o. s.o.Ar¹-200 222 s.o. s.o. s.o. Ar¹-201 223 s.o. s.o. Ar¹-200 Ar¹-200 224s.o. s.o. s.o. Ar¹-201 225 s.o. s.o. Ar¹-201 Ar¹-201 226 s.o. Ar¹-1 Ar¹-1  Ar¹-1  227 s.o. s.o. s.o. Ar¹-74  228 s.o. s.o. s.o. Ar¹-132 229s.o. s.o. s.o. Ar¹-134 230 s.o. s.o. s.o. Ar¹-136 231 s.o. s.o. s.o.Ar¹-137 232 s.o. s.o. s.o. Ar¹-165 233 s.o. s.o. s.o. Ar¹-200 234 s.o.s.o. s.o. Ar¹-201 235 s.o. s.o. Ar¹-74  Ar¹-74  236 s.o. s.o. s.o.Ar¹-132 237 s.o. s.o. s.o. Ar¹-134 238 s.o. s.o. s.o. Ar¹-136 239 s.o.s.o. s.o. Ar¹-137 240 s.o. s.o. s.o. Ar¹-165 241 s.o. s.o. s.o. Ar¹-200242 s.o. s.o. s.o. Ar¹-201 243 s.o. s.o. Ar¹-132 Ar¹-132 244 s.o. s.o.s.o. Ar¹-134 245 s.o. s.o. s.o. Ar¹-136 246 s.o. s.o. s.o. Ar¹-137 247s.o. s.o. s.o. Ar¹-165 248 s.o. s.o. s.o. Ar¹-200 249 s.o. s.o. s.o.Ar¹-201 250 s.o. s.o. Ar¹-134 Ar¹-134 251 s.o. s.o. s.o. Ar¹-136 252s.o. s.o. s.o. Ar¹-137 253 s.o. s.o. s.o. Ar¹-165 254 s.o. s.o. s.o.Ar¹-200 255 s.o. s.o. s.o. Ar¹-201 256 s.o. s.o. Ar¹-136 Ar¹-136 257s.o. s.o. s.o. Ar¹-137 258 s.o. s.o. s.o. Ar¹-165 259 s.o. s.o. s.o.Ar¹-200 260 s.o. s.o. s.o. Ar¹-201 261 s.o. s.o. Ar¹-137 Ar¹-137 262s.o. s.o. s.o. Ar¹-165 263 s.o. s.o. s.o. Ar¹-200 264 s.o. s.o. s.o.Ar¹-201 265 s.o. s.o. Ar¹-165 Ar¹-165 266 s.o. s.o. s.o. Ar¹-200 267s.o. s.o. s.o. Ar¹-201 268 s.o. s.o. Ar¹-200 Ar¹-200 269 s.o. s.o. s.o.Ar¹-201 270 s.o. s.o. Ar¹-201 Ar¹-201 271 s.o. Ar¹-2  Ar¹-1  Ar¹-1  272s.o. s.o. s.o. Ar¹-74  273 s.o. s.o. s.o. Ar¹-132 274 s.o. s.o. s.o.Ar¹-134 275 s.o. s.o. s.o. Ar¹-136 276 s.o. s.o. s.o. Ar¹-137 277 s.o.s.o. s.o. Ar¹-165 278 s.o. s.o. s.o. Ar¹-200 279 s.o. s.o. s.o. Ar¹-201280 s.o. s.o. Ar¹-74 Ar¹-74  281 s.o. s.o. s.o. Ar¹-132 282 s.o. s.o.s.o. Ar¹-134 283 s.o. s.o. s.o. Ar¹-136 284 s.o. s.o. s.o. Ar¹-137 285s.o. s.o. s.o. Ar¹-165 286 s.o. s.o. s.o. Ar¹-200 287 s.o. s.o. s.o.Ar¹-201 288 s.o. s.o. Ar¹-132 Ar¹-132 289 s.o. s.o. s.o. Ar¹-134 290s.o. s.o. s.o. Ar¹-136 291 s.o. s.o. s.o. Ar¹-137 292 s.o. s.o. s.o.Ar¹-165 293 s.o. s.o. s.o. Ar¹-200 294 s.o. s.o. s.o. Ar¹-201 295 s.o.s.o. Ar¹-134 Ar¹-134 296 s.o. s.o. s.o. Ar¹-136 297 s.o. s.o. s.o.Ar¹-137 298 s.o. s.o. s.o. Ar¹-165 299 s.o. s.o. s.o. Ar¹-200 300 s.o.s.o. s.o. Ar¹-201 301 s.o. s.o. Ar¹-136 Ar¹-136 302 s.o. s.o. s.o.Ar¹-137 303 s.o. s.o. s.o. Ar¹-165 304 s.o. s.o. s.o. Ar¹-200 305 s.o.s.o. s.o. Ar¹-201 306 s.o. s.o. Ar¹-137 Ar¹-137 307 s.o. s.o. s.o.Ar¹-165 308 s.o. s.o. s.o. Ar¹-200 309 s.o. s.o. s.o. Ar¹-201 310 s.o.s.o. s.o. Ar¹-165 311 s.o. s.o. s.o. Ar¹-200 312 s.o. s.o. s.o. Ar¹-201313 s.o. s.o. Ar¹-200 Ar¹-200 314 s.o. s.o. s.o. Ar¹-201 315 s.o. s.o.Ar¹-201 Ar¹-201 316 s.o. Ar¹-3  Ar¹-1  Ar¹-1  317 s.o. s.o. s.o. Ar¹-74 318 s.o. s.o. s.o. Ar¹-132 319 s.o. s.o. s.o. Ar¹-134 320 s.o. s.o. s.o.Ar¹-136 321 s.o. s.o. s.o. Ar¹-137 322 s.o. s.o. s.o. Ar¹-165 323 s.o.s.o. s.o. Ar¹-200 324 s.o. s.o. s.o. Ar¹-201 325 s.o. s.o. Ar¹-74 Ar¹-74  326 s.o. s.o. s.o. Ar¹-132 327 s.o. s.o. s.o. Ar¹-134 328 s.o.s.o. s.o. Ar¹-136 329 s.o. s.o. s.o. Ar¹-137 330 s.o. s.o. s.o. Ar¹-165331 s.o. s.o. s.o. Ar¹-200 332 s.o. s.o. s.o. Ar¹-201 333 s.o. s.o.Ar¹-132 Ar¹-132 334 s.o. s.o. s.o. Ar¹-134 335 s.o. s.o. s.o. Ar¹-136336 s.o. s.o. s.o. Ar¹-137 337 s.o. s.o. s.o. Ar¹-165 338 s.o. s.o. s.o.Ar¹-200 339 s.o. s.o. s.o. Ar¹-201 340 s.o. s.o. Ar¹-134 Ar¹-134 341s.o. s.o. s.o. Ar¹-136 342 s.o. s.o. s.o. Ar¹-137 343 s.o. s.o. s.o.Ar¹-165 344 s.o. s.o. s.o. Ar¹-200 345 s.o. s.o. s.o. Ar¹-201 346 s.o.s.o. Ar¹-136 Ar¹-136 347 s.o. s.o. s.o. Ar¹-137 348 s.o. s.o. s.o.Ar¹-165 349 s.o. s.o. s.o. Ar¹-200 350 s.o. s.o. s.o. Ar¹-201 351 s.o.s.o. Ar¹-137 Ar¹-137 352 s.o. s.o. s.o. Ar¹-165 353 s.o. s.o. s.o.Ar¹-200 354 s.o. s.o. s.o. Ar¹-201 355 s.o. s.o. Ar¹-165 Ar¹-165 356s.o. s.o. s.o. Ar¹-200 357 s.o. s.o. s.o. Ar¹-201 358 s.o. s.o. Ar¹-200Ar¹-200 359 s.o. s.o. s.o. Ar¹-201 360 s.o. s.o. Ar¹-201 Ar¹-201 361I-1-5-O k = 0 Ar¹-1  Ar¹-1  362 s.o. s.o. s.o. Ar¹-74  363 s.o. s.o.s.o. Ar¹-132 364 s.o. s.o. s.o. Ar¹-134 365 s.o. s.o. s.o. Ar¹-136 366s.o. s.o. s.o. Ar¹-137 367 s.o. s.o. s.o. Ar¹-165 368 s.o. s.o. s.o.Ar¹-200 369 s.o. s.o. s.o. Ar¹-201 370 s.o. s.o. Ar¹-74 Ar¹-74  371 s.o.s.o. s.o. Ar¹-132 372 s.o. s.o. s.o. Ar¹-134 373 s.o. s.o. s.o. Ar¹-136374 s.o. s.o. s.o. Ar¹-137 375 s.o. s.o. s.o. Ar¹-165 376 s.o. s.o. s.o.Ar¹-200 377 s.o. s.o. s.o. Ar¹-201 378 s.o. s.o. Ar¹-32 Ar¹-132 379 s.o.s.o. s.o. Ar¹-134 380 s.o. s.o. s.o. Ar¹-136 381 s.o. s.o. s.o. Ar¹-137382 s.o. s.o. s.o. Ar¹-165 383 s.o. s.o. s.o. Ar¹-200 384 s.o. s.o. s.o.Ar¹-201 385 s.o. s.o. Ar¹-134 Ar¹-134 386 s.o. s.o. s.o. Ar¹-136 387s.o. s.o. s.o. Ar¹-137 388 s.o. s.o. s.o. Ar¹-165 389 s.o. s.o. s.o.Ar¹-200 390 s.o. s.o. s.o. Ar¹-201 391 s.o. s.o. Ar¹-136 Ar¹-136 392s.o. s.o. s.o. Ar¹-137 393 s.o. s.o. s.o. Ar¹-165 394 s.o. s.o. s.o.Ar¹-200 395 s.o. s.o. s.o. Ar¹-201 396 s.o. s.o. Ar¹-137 Ar¹-137 397s.o. s.o. s.o. Ar¹-165 398 s.o. s.o. s.o. Ar¹-200 399 s.o. s.o. s.o.Ar¹-201 400 s.o. s.o. Ar¹-165 Ar¹-165 401 s.o. s.o. s.o. Ar¹-200 402s.o. s.o. s.o. Ar¹-201 403 s.o. s.o. Ar¹-200 Ar¹-200 404 s.o. s.o. s.o.Ar¹-201 405 s.o. s.o. Ar¹-201 Ar¹-201 406 s.o. Ar¹-1  Ar¹-1  Ar¹-1  407s.o. s.o. s.o. Ar¹-74  408 s.o. s.o. s.o. Ar¹-132 409 s.o. s.o. s.o.Ar¹-134 410 s.o. s.o. s.o. Ar¹-136 411 s.o. s.o. s.o. Ar¹-137 412 s.o.s.o. s.o. Ar¹-165 413 s.o. s.o. s.o. Ar¹-200 414 s.o. s.o. s.o. Ar¹-201415 s.o. s.o. Ar¹-74  Ar¹-74  416 s.o. s.o. s.o. Ar¹-132 417 s.o. s.o.s.o. Ar¹-134 418 s.o. s.o. s.o. Ar¹-136 419 s.o. s.o. s.o. Ar¹-137 420s.o. s.o. s.o. Ar¹-165 421 s.o. s.o. s.o. Ar¹-200 422 s.o. s.o. s.o.Ar¹-201 423 s.o. s.o. Ar¹-132 Ar¹-132 424 s.o. s.o. s.o. Ar¹-134 425s.o. s.o. s.o. Ar¹-136 426 s.o. s.o. s.o. Ar¹-137 427 s.o. s.o. s.o.Ar¹-165 428 s.o. s.o. s.o. Ar¹-200 429 s.o. s.o. s.o. Ar¹-201 430 s.o.s.o. Ar¹-134 Ar¹-134 431 s.o. s.o. s.o. Ar¹-136 432 s.o. s.o. s.o.Ar¹-137 433 s.o. s.o. s.o. Ar¹-165 434 s.o. s.o. s.o. Ar¹-200 435 s.o.s.o. s.o. Ar¹-201 436 s.o. s.o. Ar¹-136 Ar¹-136 437 s.o. s.o. s.o.Ar¹-137 438 s.o. s.o. s.o. Ar¹-165 439 s.o. s.o. s.o. Ar¹-200 440 s.o.s.o. s.o. Ar¹-201 441 s.o. s.o. Ar¹-137 Ar¹-137 442 s.o. s.o. s.o.Ar¹-165 443 s.o. s.o. s.o. Ar¹-200 444 s.o. s.o. s.o. Ar¹-201 445 s.o.s.o. Ar¹-165 Ar¹-165 446 s.o. s.o. s.o. Ar¹-200 447 s.o. s.o. s.o.Ar¹-201 448 s.o. s.o. Ar¹-200 Ar¹-200 449 s.o. s.o. s.o. Ar¹-201 450s.o. s.o. Ar¹-201 Ar¹-201 451 s.o. Ar¹-2  Ar¹-1  Ar¹-1  452 s.o. s.o.s.o. Ar¹-74  453 s.o. s.o. s.o. Ar¹-132 454 s.o. s.o. s.o. Ar¹-134 455s.o. s.o. s.o. Ar¹-136 456 s.o. s.o. s.o. Ar¹-137 457 s.o. s.o. s.o.Ar¹-165 458 s.o. s.o. s.o. Ar¹-200 459 s.o. s.o. s.o. Ar¹-201 460 s.o.s.o. Ar¹-74  Ar¹-74  461 s.o. s.o. s.o. Ar¹-132 462 s.o. s.o. s.o.Ar¹-134 463 s.o. s.o. s.o. Ar¹-136 464 s.o. s.o. s.o. Ar¹-137 465 s.o.s.o. s.o. Ar¹-165 466 s.o. s.o. s.o. Ar¹-200 467 s.o. s.o. s.o. Ar¹-201468 s.o. s.o. Ar¹-132 Ar¹-132 469 s.o. s.o. s.o. Ar¹-134 470 s.o. s.o.s.o. Ar¹-136 471 s.o. s.o. s.o. Ar¹-137 472 s.o. s.o. s.o. Ar¹-165 473s.o. s.o. s.o. Ar¹-200 474 s.o. s.o. s.o. Ar¹-201 475 s.o. s.o. Ar¹-134Ar¹-134 476 s.o. s.o. s.o. Ar¹-136 477 s.o. s.o. s.o. Ar¹-137 478 s.o.s.o. s.o. Ar¹-165 479 s.o. s.o. s.o. Ar¹-200 480 s.o. s.o. s.o. Ar¹-201481 s.o. s.o. Ar¹-136 Ar¹-136 482 s.o. s.o. s.o. Ar¹-137 483 s.o. s.o.s.o. Ar¹-165 484 s.o. s.o. s.o. Ar¹-200 485 s.o. s.o. s.o. Ar¹-201 486s.o. s.o. Ar¹-137 Ar¹-137 487 s.o. s.o. s.o. Ar¹-165 488 s.o. s.o. s.o.Ar¹-200 489 s.o. s.o. s.o. Ar¹-201 490 s.o. s.o. Ar¹-165 Ar¹-165 491s.o. s.o. s.o. Ar¹-200 492 s.o. s.o. s.o. Ar¹-201 493 s.o. s.o. Ar¹-200Ar¹-200 494 s.o. s.o. s.o. Ar¹-201 495 s.o. s.o. Ar¹-201 Ar¹-201 496s.o. Ar¹-3  Ar¹-1  Ar¹-1  497 s.o. s.o. s.o. Ar¹-74  498 s.o. s.o. s.o.Ar¹-132 499 s.o. s.o. s.o. Ar¹-134 500 s.o. s.o. s.o. Ar¹-136 501 s.o.s.o. s.o. Ar¹-137 502 s.o. s.o. s.o. Ar¹-165 503 s.o. s.o. s.o. Ar¹-200504 s.o. s.o. s.o. Ar¹-201 505 s.o. s.o. Ar¹-74  Ar¹-74  506 s.o. s.o.s.o. Ar¹-132 507 s.o. s.o. s.o. Ar¹-134 508 s.o. s.o. s.o. Ar¹-136 509s.o. s.o. s.o. Ar¹-137 510 s.o. s.o. s.o. Ar¹-165 511 s.o. s.o. s.o.Ar¹-200 512 s.o. s.o. s.o. Ar¹-201 513 s.o. s.o. Ar¹-132 Ar¹-132 514s.o. s.o. s.o. Ar¹-134 515 s.o. s.o. s.o. Ar¹-136 516 s.o. s.o. s.o.Ar¹-137 517 s.o. s.o. s.o. Ar¹-165 518 s.o. s.o. s.o. Ar¹-200 519 s.o.s.o. s.o. Ar¹-201 520 s.o. s.o. Ar¹-134 Ar¹-134 521 s.o. s.o. s.o.Ar¹-136 522 s.o. s.o. s.o. Ar¹-137 523 s.o. s.o. s.o. Ar¹-165 524 s.o.s.o. s.o. Ar¹-200 525 s.o. s.o. s.o. Ar¹-201 526 s.o. s.o. Ar¹-136Ar¹-136 527 s.o. s.o. s.o. Ar¹-137 528 s.o. s.o. s.o. Ar¹-165 529 s.o.s.o. s.o. Ar¹-200 530 s.o. s.o. s.o. Ar¹-201 531 s.o. s.o. Ar¹-137Ar¹-137 532 s.o. s.o. s.o. Ar¹-165 533 s.o. s.o. s.o. Ar¹-200 534 s.o.s.o. s.o. Ar¹-201 535 s.o. s.o. Ar¹-165 Ar¹-165 536 s.o. s.o. s.o.Ar¹-200 537 s.o. s.o. s.o. Ar¹-201 538 s.o. s.o. Ar¹-200 Ar¹-200 539s.o. s.o. s.o. Ar¹-201 540 s.o. s.o. Ar¹-201 Ar¹-201 541 I-1-7-O k = 0Ar¹-1  Ar¹-1  542 s.o. s.o. s.o. Ar¹-74 543 s.o. s.o. s.o. Ar¹-132 544s.o. s.o. s.o. Ar¹-134 545 s.o. s.o. s.o. Ar¹-136 546 s.o. s.o. s.o.Ar¹-137 547 s.o. s.o. s.o. Ar¹-165 548 s.o. s.o. s.o. Ar¹-200 549 s.o.s.o. s.o. Ar¹-201 550 s.o. s.o. Ar¹-74 Ar¹-74  551 s.o. s.o. s.o.Ar¹-132 552 s.o. s.o. s.o. Ar¹-134 553 s.o. s.o. s.o. Ar¹-136 554 s.o.s.o. s.o. Ar¹-137 555 s.o. s.o. s.o. Ar¹-165 556 s.o. s.o. s.o. Ar¹-200557 s.o. s.o. s.o. Ar¹-201 558 s.o. s.o. Ar¹-132 Ar¹-132 559 s.o. s.o.s.o. Ar¹-134 560 s.o. s.o. s.o. Ar¹-136 561 s.o. s.o. s.o. Ar¹-137 562s.o. s.o. s.o. Ar¹-165 563 s.o. s.o. s.o. Ar¹-200 564 s.o. s.o. s.o.Ar¹-201 565 s.o. s.o. Ar¹-134 Ar¹-134 566 s.o. s.o. s.o. Ar¹-136 567s.o. s.o. s.o. Ar¹-137 568 s.o. s.o. s.o. Ar¹-165 569 s.o. s.o. s.o.Ar¹-200 570 s.o. s.o. s.o. Ar¹-201 571 s.o. s.o. Ar¹-136 Ar¹-136 572s.o. s.o. s.o. Ar¹-137 573 s.o. s.o. s.o. Ar¹-165 574 s.o. s.o. s.o.Ar¹-200 575 s.o. s.o. s.o. Ar¹-201 576 s.o. s.o. Ar¹-137 Ar¹-137 577s.o. s.o. s.o. Ar¹-165 578 s.o. s.o. s.o. Ar¹-200 579 s.o. s.o. s.o.Ar¹-201 580 s.o. s.o. Ar¹-165 Ar¹-165 581 s.o. s.o. s.o. Ar¹-200 582s.o. s.o. s.o. Ar¹-201 583 s.o. s.o. Ar¹-200 Ar¹-200 584 s.o. s.o. s.o.Ar¹-201 585 s.o. s.o. Ar¹-201 Ar¹-201 586 s.o. Ar¹-1  Ar¹-1  Ar¹-1  587s.o. s.o. s.o. Ar¹-74  588 s.o. s.o. s.o. Ar¹-132 589 s.o. s.o. s.o.Ar¹-134 590 s.o. s.o. s.o. Ar¹-136 591 s.o. s.o. s.o. Ar¹-137 592 s.o.s.o. s.o. Ar¹-165 593 s.o. s.o. s.o. Ar¹-200 594 s.o. s.o. s.o. Ar¹-201595 s.o. s.o. Ar¹-74  Ar¹-74  596 s.o. s.o. s.o. Ar¹-132 597 s.o. s.o.s.o. Ar¹-134 598 s.o. s.o. s.o. Ar¹-136 599 s.o. s.o. s.o. Ar¹-137 600s.o. s.o. s.o. Ar¹-165 601 s.o. s.o. s.o. Ar¹-200 602 s.o. s.o. s.o.Ar¹-201 603 s.o. s.o. Ar¹-132 Ar¹-132 604 s.o. s.o. s.o. Ar¹-134 605s.o. s.o. s.o. Ar¹-136 606 s.o. s.o. s.o. Ar¹-137 607 s.o. s.o. s.o.Ar¹-165 608 s.o. s.o. s.o. Ar¹-200 609 s.o. s.o. s.o. Ar¹-201 610 s.o.s.o. Ar¹-134 Ar¹-134 611 s.o. s.o. s.o. Ar¹-136 612 s.o. s.o. s.o.Ar¹-137 613 s.o. s.o. s.o. Ar¹-165 614 s.o. s.o. s.o. Ar¹-200 615 s.o.s.o. s.o. Ar¹-201 616 s.o. s.o. Ar¹-136 Ar¹-136 617 s.o. s.o. s.o.Ar¹-137 618 s.o. s.o. s.o. Ar¹-165 619 s.o. s.o. s.o. Ar¹-200 620 s.o.s.o. s.o. Ar¹-201 621 s.o. s.o. Ar¹-137 Ar¹-137 622 s.o. s.o. s.o.Ar¹-165 623 s.o. s.o. s.o. Ar¹-200 624 s.o. s.o. s.o. Ar¹-201 625 s.o.s.o. Ar¹-165 Ar¹-165 626 s.o. s.o. s.o. Ar¹-200 627 s.o. s.o. s.o.Ar¹-201 628 s.o. s.o. s.o. Ar¹-200 629 s.o. s.o. s.o. Ar¹-201 630 s.o.s.o. Ar¹-201 Ar¹-201 631 s.o. Ar¹-2  Ar¹-1  Ar¹-1  632 s.o. s.o. s.o.Ar¹-74  633 s.o. s.o. s.o. Ar¹-132 634 s.o. s.o. s.o. Ar¹-134 635 s.o.s.o. s.o. Ar¹-136 636 s.o. s.o. s.o. Ar¹-137 637 s.o. s.o. s.o. Ar¹-165638 s.o. s.o. s.o. Ar¹-200 639 s.o. s.o. s.o. Ar¹-201 640 s.o. s.o.Ar¹-74  Ar¹-74  641 s.o. s.o. s.o. Ar¹-132 642 s.o. s.o. s.o. Ar¹-134643 s.o. s.o. s.o. Ar¹-136 644 s.o. s.o. s.o. Ar¹-137 645 s.o. s.o. s.o.Ar¹-165 646 s.o. s.o. s.o. Ar¹-200 647 s.o. s.o. s.o. Ar¹-201 648 s.o.s.o. Ar¹-132 Ar¹-132 649 s.o. s.o. s.o. Ar¹-134 650 s.o. s.o. s.o.Ar¹-136 651 s.o. s.o. s.o. Ar¹-137 652 s.o. s.o. s.o. Ar¹-165 653 s.o.s.o. s.o. Ar¹-200 654 s.o. s.o. s.o. Ar¹-201 655 s.o. s.o. Ar¹-134Ar¹-134 656 s.o. s.o. s.o. Ar¹-136 657 s.o. s.o. s.o. Ar¹-137 658 s.o.s.o. s.o. Ar¹-165 659 s.o. s.o. s.o. Ar¹-200 660 s.o. s.o. s.o. Ar¹-201661 s.o. s.o. Ar¹-136 Ar¹-136 662 s.o. s.o. s.o. Ar¹-137 663 s.o. s.o.s.o. Ar¹-165 664 s.o. s.o. s.o. Ar¹-200 665 s.o. s.o. s.o. Ar¹-201 666s.o. s.o. Ar¹-137 Ar¹-137 667 s.o. s.o. s.o. Ar¹-165 668 s.o. s.o. s.o.Ar¹-200 669 s.o. s.o. s.o. Ar¹-201 670 s.o. s.o. Ar¹-165 Ar¹-165 671s.o. s.o. s.o. Ar¹-200 672 s.o. s.o. s.o. Ar¹-201 673 s.o. s.o. Ar¹-200Ar¹-200 674 s.o. s.o. s.o. Ar¹-201 675 s.o. s.o. Ar¹-201 Ar¹-201 676s.o. Ar¹-3  Ar¹-1  Ar¹-1  677 s.o. s.o. s.o. Ar¹-74  678 s.o. s.o. s.o.Ar¹-132 679 s.o. s.o. s.o. Ar¹-134 680 s.o. s.o. s.o. Ar¹-136 681 s.o.s.o. s.o. Ar¹-137 682 s.o. s.o. s.o. Ar¹-165 683 s.o. s.o. s.o. Ar¹-200684 s.o. s.o. s.o. Ar¹-201 685 s.o. s.o. Ar¹-74  Ar¹-74  686 s.o. s.o.s.o. Ar¹-132 687 s.o. s.o. s.o. Ar¹-134 688 s.o. s.o. s.o. 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Ar¹-132 1047 s.o. s.o. s.o. Ar¹-134 1048 s.o. s.o. s.o. Ar¹-1361049 s.o. s.o. s.o. Ar¹-137 1050 s.o. s.o. s.o. Ar¹-165 1051 s.o. s.o.s.o. Ar¹-200 1052 s.o. s.o. s.o. Ar¹-201 1053 s.o. s.o. Ar¹-132 Ar¹-1321054 s.o. s.o. s.o. Ar¹-134 1055 s.o. s.o. s.o. Ar¹-136 1056 s.o. s.o.s.o. Ar¹-137 1057 s.o. s.o. s.o. Ar¹-165 1058 s.o. s.o. s.o. Ar¹-2001059 s.o. s.o. s.o. Ar¹-201 1060 s.o. s.o. Ar¹-134 Ar¹-134 1061 s.o.s.o. s.o. Ar¹-136 1062 s.o. s.o. s.o. Ar¹-137 1063 s.o. s.o. s.o.Ar¹-165 1064 s.o. s.o. s.o. Ar¹-200 1065 s.o. s.o. s.o. Ar¹-201 1066s.o. s.o. Ar¹-136 Ar¹-136 1067 s.o. s.o. s.o. Ar¹-137 1068 s.o. s.o.s.o. Ar¹-165 1069 s.o. s.o. s.o. Ar¹-200 1070 s.o. s.o. s.o. Ar¹-2011071 s.o. s.o. Ar¹-137 Ar¹-137 1072 s.o. s.o. s.o. Ar¹-165 1073 s.o.s.o. s.o. Ar¹-200 1074 s.o. s.o. s.o. Ar¹-201 1075 s.o. s.o. Ar¹-165Ar¹-165 1076 s.o. s.o. s.o. Ar¹-200 1077 s.o. s.o. s.o. Ar¹-201 1078s.o. s.o. Ar¹-200 Ar¹-200 1079 s.o. s.o. s.o. Ar¹-201 1080 s.o. s.o.Ar¹-201 Ar¹-201 1081 I-1-5-S k = 0 Ar¹-1  Ar¹-1  1082 s.o. s.o. s.o.Ar¹-74  1083 s.o. s.o. s.o. Ar¹-132 1084 s.o. s.o. s.o. Ar¹-134 1085s.o. s.o. s.o. Ar¹-136 1086 s.o. s.o. s.o. Ar¹-137 1087 s.o. s.o. s.o.Ar¹-165 1088 s.o. s.o. s.o. Ar¹-200 1089 s.o. s.o. s.o. Ar¹-201 1090s.o. s.o. Ar¹-74  Ar¹-74  1091 s.o. s.o. s.o. Ar¹-132 1092 s.o. s.o.s.o. Ar¹-134 1093 s.o. s.o. s.o. Ar¹-136 1094 s.o. s.o. s.o. Ar¹-1371095 s.o. s.o. s.o. Ar¹-165 1096 s.o. s.o. s.o. Ar¹-200 1097 s.o. s.o.s.o. Ar¹-201 1098 s.o. s.o. Ar¹-132 Ar¹-132 1099 s.o. s.o. s.o. Ar¹-1341100 s.o. s.o. s.o. Ar¹-136 1101 s.o. s.o. s.o. Ar¹-137 1102 s.o. s.o.s.o. Ar¹-165 1103 s.o. s.o. s.o. Ar¹-200 1104 s.o. s.o. s.o. Ar¹-2011105 s.o. s.o. Ar¹-134 Ar¹-134 1106 s.o. s.o. s.o. Ar¹-136 1107 s.o.s.o. s.o. Ar¹-137 1108 s.o. s.o. s.o. Ar¹-165 1109 s.o. s.o. s.o.Ar¹-200 1110 s.o. s.o. s.o. Ar¹-201 1111 s.o. s.o. Ar¹-136 Ar¹-136 1112s.o. s.o. s.o. Ar¹-137 1113 s.o. s.o. s.o. Ar¹-165 1114 s.o. s.o. s.o.Ar¹-200 1115 s.o. s.o. s.o. Ar¹-201 1116 s.o. s.o. Ar¹-137 Ar¹-137 1117s.o. s.o. s.o. Ar¹-165 1118 s.o. s.o. s.o. Ar¹-200 1119 s.o. s.o. s.o.Ar¹-201 1120 s.o. s.o. Ar¹-165 Ar¹-165 1121 s.o. s.o. s.o. Ar¹-200 1122s.o. s.o. s.o. Ar¹-201 1123 s.o. s.o. Ar¹-200 Ar¹-200 1124 s.o. s.o.s.o. Ar¹-201 1125 s.o. s.o. Ar¹-201 Ar¹-201 1126 s.o. Ar¹-1  Ar¹-1 Ar¹-1  1127 s.o. s.o. s.o. Ar¹-74  1128 s.o. s.o. s.o. Ar¹-132 1129 s.o.s.o. s.o. Ar¹-134 1130 s.o. s.o. s.o. Ar¹-136 1131 s.o. s.o. s.o.Ar¹-137 1132 s.o. s.o. s.o. Ar¹-165 1133 s.o. s.o. s.o. Ar¹-200 1134s.o. s.o. s.o. Ar¹-201 1135 s.o. s.o. Ar¹-74 Ar¹-74 1136 s.o. s.o. s.o.Ar¹-132 1137 s.o. s.o. s.o. Ar¹-134 1138 s.o. s.o. s.o. Ar¹-136 1139s.o. s.o. s.o. Ar¹-137 1140 s.o. s.o. s.o. Ar¹-165 1141 s.o. s.o. s.o.Ar¹-200 1142 s.o. s.o. s.o. Ar¹-201 1143 s.o. s.o. Ar¹-132 Ar¹-132 1144s.o. s.o. s.o. Ar¹-134 1145 s.o. s.o. s.o. Ar¹-136 1146 s.o. s.o. s.o.Ar¹-137 1147 s.o. s.o. s.o. Ar¹-165 1148 s.o. s.o. s.o. Ar¹-200 1149s.o. s.o. s.o. Ar¹-201 1150 s.o. s.o. Ar¹-134 Ar¹-134 1151 s.o. s.o.s.o. Ar¹-136 1152 s.o. s.o. s.o. Ar¹-137 1153 s.o. s.o. s.o. Ar¹-1651154 s.o. s.o. s.o. Ar¹-200 1155 s.o. s.o. s.o. Ar¹-201 1156 s.o. s.o.Ar¹-136 Ar¹-136 1157 s.o. s.o. s.o. Ar¹-137 1158 s.o. s.o. s.o. Ar¹-1651159 s.o. s.o. s.o. Ar¹-200 1160 s.o. s.o. s.o. Ar¹-201 1161 s.o. s.o.Ar¹-137 Ar¹-137 1162 s.o. s.o. s.o. Ar¹-165 1163 s.o. s.o. s.o. Ar¹-2001164 s.o. s.o. s.o. Ar¹-201 1165 s.o. s.o. Ar¹-165 Ar¹-165 1166 s.o.s.o. s.o. Ar¹-200 1167 s.o. s.o. s.o. Ar¹-201 1168 s.o. s.o. s.o.Ar¹-200 1169 s.o. s.o. s.o. Ar¹-201 1170 s.o. s.o. Ar¹-201 Ar¹-201 1171s.o. Ar¹-2  Ar¹-1  Ar¹-1  1172 s.o. s.o. s.o. Ar¹-74  1173 s.o. s.o.s.o. Ar¹-132 1174 s.o. s.o. s.o. Ar¹-134 1175 s.o. s.o. s.o. Ar¹-1361176 s.o. s.o. s.o. Ar¹-137 1177 s.o. s.o. s.o. Ar¹-165 1178 s.o. s.o.s.o. Ar¹-200 1179 s.o. s.o. s.o. Ar¹-201 1180 s.o. s.o. Ar¹-74  Ar¹-74 1181 s.o. s.o. s.o. Ar¹-132 1182 s.o. s.o. s.o. Ar¹-134 1183 s.o. s.o.s.o. Ar¹-136 1184 s.o. s.o. s.o. Ar¹-137 1185 s.o. s.o. s.o. Ar¹-1651186 s.o. s.o. s.o. Ar¹-200 1187 s.o. s.o. s.o. Ar¹-201 1188 s.o. s.o.Ar¹-132 Ar¹-132 1189 s.o. s.o. s.o. Ar¹-134 1190 s.o. s.o. s.o. Ar¹-1361191 s.o. s.o. s.o. Ar¹-137 1192 s.o. s.o. s.o. Ar¹-165 1193 s.o. s.o.s.o. Ar¹-200 1194 s.o. s.o. s.o. Ar¹-201 1195 s.o. s.o. Ar¹-134 Ar¹-1341196 s.o. s.o. s.o. Ar¹-136 1197 s.o. s.o. s.o. Ar¹-137 1198 s.o. s.o.s.o. Ar¹-165 1199 s.o. s.o. s.o. Ar¹-200 1200 s.o. s.o. s.o. Ar¹-2011201 s.o. s.o. Ar¹-136 Ar¹-136 1202 s.o. s.o. s.o. Ar¹-137 1203 s.o.s.o. s.o. Ar¹-165 1204 s.o. s.o. s.o. Ar¹-200 1205 s.o. s.o. s.o.Ar¹-201 1206 s.o. s.o. Ar¹-137 Ar¹-137 1207 s.o. s.o. s.o. Ar¹-165 1208s.o. s.o. s.o. Ar¹-200 1209 s.o. s.o. s.o. Ar¹-201 1210 s.o. s.o.Ar¹-165 Ar¹-165 1211 s.o. s.o. s.o. Ar¹-200 1212 s.o. s.o. s.o. Ar¹-2011213 s.o. s.o. s.o. Ar¹-200 1214 s.o. s.o. s.o. Ar¹-201 1215 s.o. s.o.Ar¹-201 Ar¹-201 1216 s.o. Ar¹-3  Ar¹-1  Ar¹-1  1217 s.o. s.o. s.o.Ar¹-74  1218 s.o. s.o. s.o. Ar¹-132 1219 s.o. s.o. s.o. Ar¹-134 1220s.o. s.o. s.o. Ar¹-136 1221 s.o. s.o. s.o. Ar¹-137 1222 s.o. s.o. s.o.Ar¹-165 1223 s.o. s.o. s.o. Ar¹-200 1224 s.o. s.o. s.o. Ar¹-201 1225s.o. s.o. Ar¹-74  Ar¹-74  1226 s.o. s.o. s.o. Ar¹-132 1227 s.o. s.o.s.o. Ar¹-134 1228 s.o. s.o. s.o. Ar¹-136 1229 s.o. s.o. s.o. Ar¹-1371230 s.o. s.o. s.o. Ar¹-165 1231 s.o. s.o. s.o. Ar¹-200 1232 s.o. s.o.s.o. Ar¹-201 1233 s.o. s.o. Ar¹-132 Ar¹-132 1234 s.o. s.o. s.o. Ar¹-1341235 s.o. s.o. s.o. Ar¹-136 1236 s.o. s.o. s.o. Ar¹-137 1237 s.o. s.o.s.o. Ar¹-165 1238 s.o. s.o. s.o. Ar¹-200 1239 s.o. s.o. s.o. Ar¹-2011240 s.o. s.o. Ar¹-134 Ar¹-134 1241 s.o. s.o. s.o. Ar¹-136 1242 s.o.s.o. s.o. Ar¹-137 1243 s.o. s.o. s.o. Ar¹-165 1244 s.o. s.o. s.o.Ar¹-200 1245 s.o. s.o. s.o. Ar¹-201 1246 s.o. s.o. Ar¹-136 Ar¹-136 1247s.o. s.o. s.o. Ar¹-137 1248 s.o. s.o. s.o. Ar¹-165 1249 s.o. s.o. s.o.Ar¹-200 1250 s.o. s.o. s.o. Ar¹-201 1251 s.o. s.o. Ar¹-137 Ar¹-137 1252s.o. s.o. s.o. Ar¹-165 1253 s.o. s.o. s.o. Ar¹-200 1254 s.o. s.o. s.o.Ar¹-201 1255 s.o. s.o. Ar¹-165 Ar¹-165 1256 s.o. s.o. s.o. Ar¹-200 1257s.o. s.o. s.o. Ar¹-201 1258 s.o. s.o. s.o. Ar¹-200 1259 s.o. s.o. s.o.Ar¹-201 1260 s.o. s.o. Ar¹-201 Ar¹-201 1261 I-1-7-O k = 0 Ar¹-1  Ar¹-1 1262 s.o. s.o. s.o. Ar¹-74 1263 s.o. s.o. s.o. Ar¹-132 1264 s.o. s.o.s.o. Ar¹-134 1265 s.o. s.o. s.o. Ar¹-136 1266 s.o. s.o. s.o. Ar¹-1371267 s.o. s.o. s.o. Ar¹-165 1268 s.o. s.o. s.o. Ar¹-200 1269 s.o. s.o.s.o. Ar¹-201 1270 s.o. s.o. Ar¹-74  Ar¹-74  1271 s.o. s.o. s.o. Ar¹-1321272 s.o. s.o. s.o. Ar¹-134 1273 s.o. s.o. s.o. Ar¹-136 1274 s.o. s.o.s.o. Ar¹-137 1275 s.o. s.o. s.o. Ar¹-165 1276 s.o. s.o. s.o. Ar¹-2001277 s.o. s.o. s.o. Ar¹-201 1278 s.o. s.o. Ar¹-132 Ar¹-132 1279 s.o.s.o. s.o. Ar¹-134 1280 s.o. s.o. s.o. Ar¹-136 1281 s.o. s.o. s.o.Ar¹-137 1282 s.o. s.o. s.o. Ar¹-165 1283 s.o. s.o. s.o. Ar¹-200 1284s.o. s.o. s.o. Ar¹-201 1285 s.o. s.o. Ar¹-134 Ar¹-134 1286 s.o. s.o.s.o. Ar¹-136 1287 s.o. s.o. s.o. Ar¹-137 1288 s.o. s.o. s.o. Ar¹-1651289 s.o. s.o. s.o. Ar¹-200 1290 s.o. s.o. s.o. Ar¹-201 1291 s.o. s.o.Ar¹-136 Ar¹-136 1292 s.o. s.o. s.o. Ar¹-137 1293 s.o. s.o. s.o. Ar¹-1651294 s.o. s.o. s.o. Ar¹-200 1295 s.o. s.o. s.o. Ar¹-201 1296 s.o. s.o.Ar¹-137 Ar¹-137 1297 s.o. s.o. s.o. Ar¹-165 1298 s.o. s.o. s.o. Ar¹-2001299 s.o. s.o. s.o. Ar¹-201 1300 s.o. s.o. Ar¹-165 Ar¹-165 1301 s.o.s.o. s.o. Ar¹-200 1302 s.o. s.o. s.o. Ar¹-201 1303 s.o. s.o. Ar¹-200Ar¹-200 1304 s.o. s.o. s.o. Ar¹-201 1305 s.o. s.o. Ar¹-201 Ar¹-201 1306s.o. Ar¹-1  Ar¹-1  Ar¹-1  1307 s.o. s.o. s.o. Ar¹-74  1308 s.o. s.o.s.o. Ar¹-132 1309 s.o. s.o. s.o. Ar¹-134 1310 s.o. s.o. s.o. Ar¹-1361311 s.o. s.o. s.o. Ar¹-137 1312 s.o. s.o. s.o. Ar¹-165 1313 s.o. s.o.s.o. Ar¹-200 1314 s.o. s.o. s.o. Ar¹-201 1315 s.o. s.o. Ar¹-74  Ar¹-74 1316 s.o. s.o. s.o. Ar¹-132 1317 s.o. s.o. s.o. Ar¹-134 1318 s.o. s.o.s.o. Ar¹-136 1319 s.o. s.o. s.o. Ar¹-137 1320 s.o. s.o. s.o. Ar¹-1651321 s.o. s.o. s.o. Ar¹-200 1322 s.o. s.o. s.o. Ar¹-201 1323 s.o. s.o.Ar¹-132 Ar¹-132 1324 s.o. s.o. s.o. Ar¹-134 1325 s.o. s.o. s.o. Ar¹-1361326 s.o. s.o. s.o. Ar¹-137 1327 s.o. s.o. s.o. Ar¹-165 1328 s.o. s.o.s.o. Ar¹-200 1329 s.o. s.o. s.o. Ar¹-201 1330 s.o. s.o. Ar¹-134 Ar¹-1341331 s.o. s.o. s.o. Ar¹-136 1332 s.o. s.o. s.o. Ar¹-137 1333 s.o. s.o.s.o. Ar¹-165 1334 s.o. s.o. s.o. Ar¹-200 1335 s.o. s.o. s.o. Ar¹-2011336 s.o. s.o. Ar¹-136 Ar¹-136 1337 s.o. s.o. s.o. Ar¹-137 1338 s.o.s.o. s.o. Ar¹-165 1339 s.o. s.o. s.o. Ar¹-200 1340 s.o. s.o. s.o.Ar¹-201 1341 s.o. s.o. Ar¹-137 Ar¹-137 1342 s.o. s.o. s.o. Ar¹-165 1343s.o. s.o. s.o. Ar¹-200 1344 s.o. s.o. s.o. Ar¹-201 1345 s.o. s.o.Ar¹-165 Ar¹-165 1346 s.o. s.o. s.o. Ar¹-200 1347 s.o. s.o. s.o. Ar¹-2011348 s.o. s.o. Ar¹-200 Ar¹-200 1349 s.o. s.o. s.o. Ar¹-201 1350 s.o.s.o. Ar¹-201 Ar¹-201 1351 s.o. Ar¹-2  Ar¹-1  Ar¹-1  1352 s.o. s.o. s.o.Ar¹-74  1353 s.o. s.o. s.o. Ar¹-132 1354 s.o. s.o. s.o. Ar¹-134 1355s.o. s.o. s.o. Ar¹-136 1356 s.o. s.o. s.o. Ar¹-137 1357 s.o. s.o. s.o.Ar¹-165 1358 s.o. s.o. s.o. Ar¹-200 1359 s.o. s.o. s.o. Ar¹-201 1360s.o. s.o. Ar¹-74  Ar¹-74  1361 s.o. s.o. s.o. Ar¹-132 1362 s.o. s.o.s.o. Ar¹-134 1363 s.o. s.o. s.o. Ar¹-136 1364 s.o. s.o. s.o. Ar¹-1371365 s.o. s.o. s.o. Ar¹-165 1366 s.o. s.o. s.o. Ar¹-200 1367 s.o. s.o.s.o. Ar¹-201 1368 s.o. s.o. Ar¹-132 Ar¹-132 1369 s.o. s.o. s.o. Ar¹-1341370 s.o. s.o. s.o. Ar¹-136 1371 s.o. s.o. s.o. Ar¹-137 1372 s.o. s.o.s.o. Ar¹-165 1373 s.o. s.o. s.o. Ar¹-200 1374 s.o. s.o. s.o. Ar¹-2011375 s.o. s.o. Ar¹-134 Ar¹-134 1376 s.o. s.o. s.o. Ar¹-136 1377 s.o.s.o. s.o. Ar¹-137 1378 s.o. s.o. s.o. Ar¹-165 1379 s.o. s.o. s.o.Ar¹-200 1380 s.o. s.o. s.o. Ar¹-201 1381 s.o. s.o. Ar¹-136 Ar¹-136 1382s.o. s.o. s.o. Ar¹-137 1383 s.o. s.o. s.o. Ar¹-165 1384 s.o. s.o. s.o.Ar¹-200 1385 s.o. s.o. s.o. Ar¹-201 1386 s.o. s.o. Ar¹-137 Ar¹-137 1387s.o. s.o. s.o. Ar¹-165 1388 s.o. s.o. s.o. Ar¹-200 1389 s.o. s.o. s.o.Ar¹-201 1390 s.o. s.o. Ar¹-165 Ar¹-165 1391 s.o. s.o. s.o. Ar¹-200 1392s.o. s.o. s.o. Ar¹-201 1393 s.o. s.o. Ar¹-200 Ar¹-200 1394 s.o. s.o.s.o. Ar¹-201 1395 s.o. s.o. Ar¹-201 Ar¹-201 1396 s.o. Ar¹-3  Ar¹-1 Ar¹-1  1397 s.o. s.o. s.o. Ar¹-74  1398 s.o. s.o. s.o. Ar¹-132 1399 s.o.s.o. s.o. Ar¹-134 1400 s.o. s.o. s.o. Ar¹-136 1401 s.o. s.o. s.o.Ar¹-137 1402 s.o. s.o. s.o. Ar¹-165 1403 s.o. s.o. s.o. Ar¹-200 1404s.o. s.o. s.o. Ar¹-201 1405 s.o. s.o. Ar¹-74  Ar¹-74  1406 s.o. s.o.s.o. Ar¹-132 1407 s.o. s.o. s.o. Ar¹-134 1408 s.o. s.o. s.o. Ar¹-1361409 s.o. s.o. s.o. Ar¹-137 1410 s.o. s.o. s.o. Ar¹-165 1411 s.o. s.o.s.o. Ar¹-200 1412 s.o. s.o. s.o. Ar¹-201 1413 s.o. s.o. Ar¹-132 Ar¹-1321414 s.o. s.o. s.o. Ar¹-134 1415 s.o. s.o. s.o. Ar¹-136 1416 s.o. s.o.s.o. Ar¹-137 1417 s.o. s.o. s.o. Ar¹-165 1418 s.o. s.o. s.o. Ar¹-2001419 s.o. s.o. s.o. Ar¹-201 1420 s.o. s.o. Ar¹-134 Ar¹-134 1421 s.o.s.o. s.o. Ar¹-136 1422 s.o. s.o. s.o. Ar¹-137 1423 s.o. s.o. s.o.Ar¹-165 1424 s.o. s.o. s.o. Ar¹-200 1425 s.o. s.o. s.o. Ar¹-201 1426s.o. s.o. Ar¹-136 Ar¹-136 1427 s.o. s.o. s.o. Ar¹-137 1428 s.o. s.o.s.o. Ar¹-165 1429 s.o. s.o. s.o. Ar¹-200 1430 s.o. s.o. s.o. Ar¹-2011431 s.o. s.o. Ar¹-137 Ar¹-137 1432 s.o. s.o. s.o. Ar¹-165 1433 s.o.s.o. s.o. Ar¹-200 1434 s.o. s.o. s.o. Ar¹-201 1435 s.o. s.o. Ar¹-165Ar¹-165 1436 s.o. s.o. s.o. Ar¹-200 1437 s.o. s.o. s.o. Ar¹-201 1438s.o. s.o. Ar¹-200 Ar¹-200 1439 s.o. s.o. s.o. Ar¹-201 1440 s.o. s.o.Ar¹-201 Ar¹-201

The base skeletons specified in the table, which are also generallyparticularly preferred embodiments of compounds of the formula (I), areas follows:

Preferred compounds of the formula (I) are additionally shown in thefollowing table:

72

For the synthesis of the compounds of the formula (I), it is possible toutilize methods known in the prior art, especially methods disclosed inpublished specification WO 2014/072017.

The device of the invention is preferably selected from the groupconsisting of organic integrated circuits (OICs), organic field-effecttransistors (OFETs), organic thin-film transistors (OTFTs), organiclight-emitting transistors (OLETs), organic solar cells (OSCs), organicoptical detectors, organic photoreceptors, organic field-quench devices(OFQDs), organic light-emitting electrochemical cells (OLECs), organiclaser diodes (O-lasers) and organic electroluminescent devices (OLEDs).It is more preferably an organic electroluminescent device.

In the electronic device of the invention, the compound of the formula(I) is preferably present in a layer arranged adjacent to the anode.This layer preferably comprises a p-dopant. p-Dopants used according tothe present invention are preferably those organic electron acceptorcompounds capable of oxidizing one or more of the other compounds in themixture.

Particularly preferred embodiments of p-dopants are the compoundsdisclosed in WO 2011/073149, EP 1968131, EP 2276085, EP 2213662, EP1722602, EP 2045848, DE 102007031220, U.S. Pat. Nos. 8,044,390,8,057,712, WO 2009/003455, WO 2010/094378, WO 2011/120709, US2010/0096600, WO 2012/095143 and DE 102012209523.

Particularly preferred p-dopants are quinodimethane compounds,azaindenofluorenediones, azaphenalenes, azatriphenylenes, 12, metalhalides, preferably transition metal halides, metal oxides, preferablymetal oxides containing at least one transition metal or a metal of maingroup 3, and transition metal complexes, preferably complexes of Cu, Co,Ni, Pd and Pt with ligands containing at least one oxygen atom asbonding site.

Preference is further given to transition metal oxides as dopants,preferably oxides of rhenium, molybdenum and tungsten, more preferablyRe₂O₇, MoO₃, WO₃ and ReO₃.

The p-dopants are preferably in substantially homogeneous distributionin the p-doped layers. This can be achieved, for example, bycoevaporation of the p-dopant and the hole transport material matrix.Preferably, p-dopants are present in the layer in question in a totalproportion of 0.5% to 10% by volume, preferably 0.8% to 8% by volume.

Preferred p-dopants are especially the following compounds;

In addition, it is preferable that, as a further feature of theelectronic device of the invention, there is at least one further layerthat does not include any compound of the formula (I) between the layercomprising the compound of the formula (I) and the emitting layerclosest to the anode.

It is preferable that the layer that adjoins the emitting layer closestto the anode on the anode side does not include any compound of theformula (I).

Preferably, the device fulfils both the abovementioned conditions a) andb):

-   -   a) the hole-transporting layer directly adjoins the anode; and    -   b) there are at least two further layers arranged between the        hole-transporting layer and the emitting layer, and there are no        further emitting layers arranged between the emitting layer and        the anode.

Preference is given to an electronic device comprising the followinglayers in the sequence mentioned: anode, hole-transporting layer HTL1,hole-transporting layer HTL2, hole-transporting layer HTL3, emittinglayer EML, electron-transporting layer ETL, and cathode, where furtherlayers may be present, where the layer HTL1 adjoins the anode, where thelayer HTL3 adjoins the emitting layer, and where the layer HTL1comprises a compound of the formula (I). Preferably, at the same time,the layer HTL3 does not include any compound of the formula (I).

A particularly preferred embodiment of the device has the followinglayer sequence between the anode and the emitting layer closest to theanode: anode, hole-transporting layer HTL1 comprising a compound of theformula (I), hole-transporting layer HTL2, hole-transporting layer HTL3not comprising any compound of the formula (I), emitting layer closestto the anode. In this case, there are preferably no further layersbetween the anode and the emitting layer closest to the anode. The layerHTL1 here preferably has a thickness of 5 to 50 nm. The layer HTL2 herepreferably has a thickness of 5 to 250 nm. The layer HTL3 herepreferably has a thickness of 5 to 120 nm.

An alternative particularly preferred embodiment of the device has thefollowing layer sequence between the anode and the emitting layerclosest to the anode: anode, hole-transporting layer HTL1 comprising acompound of the formula (I) and a p-dopant, hole-transporting layerHTL2, hole-transporting layer HTL3 not comprising any compound of theformula (I), emitting layer closest to the anode. In this case, thereare preferably no further layers between the anode and the emittinglayer closest to the anode. The layer HTL1 here preferably has athickness of 5 to 250 nm. The layer HTL2 here preferably has a thicknessof 5 to 250 nm. The layer HTL3 here preferably has a thickness of 5 to120 nm.

An alternative particularly preferred embodiment of the device has thefollowing layer sequence between the anode and the emitting layerclosest to the anode: anode, hole-transporting layer HTL1 comprising acompound of the formula (I) and a p-dopant, hole-transporting layerHTL2a, hole-transporting layer HTL2b comprising a p-dopant,hole-transporting layer HTL3 not comprising any compound of the formula(I), emitting layer closest to the anode. In this case, there arepreferably no further layers between the anode and the emitting layerclosest to the anode.

The hole-transporting layer that adjoins the emitting layer closest tothe anode on the anode side preferably comprises a monoamine compound. Amonoamine compound is understood here to mean a compound containing onlyone amino group. Preferably, this amino group is a diarylamino group. Adiarylamino group is understood to mean a group in which there are twogroups selected from aryl groups and heteroaryl groups bonded to theamino nitrogen atom.

More preferably, the hole-transporting layer adjoining the emittinglayer closest to the anode on the anode side comprises a monoaminecompound containing at least one group selected from spirobifluorenylgroups, phenanthrenyl groups, fluorenyl groups, carbazolyl groups,dibenzofuranyl groups and dibenzothiophenyl groups. Among these,particular preference is given to spirobifluorenylmonoamines bearing adiarylamino group at one of positions 1, 3 and 4 on the spirobifluorenebase skeleton, especially including the compounds disclosed in publishedspecification WO 2013/120577 on pages 36-51 and 88-122. Very particularpreference is given to spirobifluorenylmonoamines bearing a diarylaminogroup at position 4 on the spirobifluorene base skeleton, especiallyincluding the compounds disclosed in published specification WO2013/120577 on pages 36-51 and 88-122.

It is preferable that the monoamine compound present in thehole-transporting layer that adjoins the emitting layer closest to theanode on the anode side has a HOMO energy level of 5.0 to 5.6 eV, morepreferably 5.1 to 5.5 eV. The HOMO energy level is determined here bymeans of cyclic voltammetry (CV), by the method described at page 28line 1 to page 29 line 21 of the published specification WO 2011/032624.

The device may, in addition to the layers mentioned, have furtherlayers, especially including layers selected from hole injection layers,hole transport layers, hole blocker layers, electron transport layers,electron injection layers, electron blocker layers, exciton blockerlayers, interlayers, charge generation layers and organic or inorganicp/n junctions.

The device preferably comprises only one emitting layer. However, it mayalso comprise two or more emitting layers. In this case, these multipleemitting layers preferably have multiple emission maxima between 380 nmand 750 nm overall, such that the overall result is white emission; inother words, various emitting compounds which may fluoresce orphosphoresce and which emit blue, green, yellow, orange or red light areused in the emitting layers. Especially preferred are three-layersystems, i.e. systems having three emitting layers, where the threelayers show blue, green and orange or red emission.

The emitting layer of the device may be a fluorescent emitting layer, orit may be a phosphorescent emitting layer.

Phosphorescent emitting layers are especially understood to mean layerscomprising at least one phosphorescent emitter. The term “phosphorescentemitters” encompasses compounds where the light is emitted through aspin-forbidden transition, for example a transition from an excitedtriplet state or a state having a higher spin quantum number, forexample a quintet state.

Suitable phosphorescent emitters (=triplet emitters) are especiallycompounds which, when suitably excited, emit light, preferably in thevisible region, and also contain at least one atom of atomic numbergreater than 20, preferably greater than 38, and less than 84, morepreferably greater than 56 and less than 80. Preference is given tousing, as phosphorescent emitters, compounds containing copper,molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium,palladium, platinum, silver, gold or europium, especially compoundscontaining iridium, platinum or copper. In the context of the presentinvention, all luminescent iridium, platinum or copper complexes areconsidered to be phosphorescent emitters.

Preferably, the phosphorescent emitting layer of the device is a green-or red-phosphorescing layer. In addition, the fluorescent emitting layerof the device is preferably a blue-fluorescing layer.

The emitting layers preferably comprise at least one matrix material andat least one emitter.

Especially in the case of phosphorescent emitting layers, it ispreferable that the layer in question comprises two or more differentmatrix materials, preferably two or three and most preferably two (mixedmatrix systems). Preferably, in this case, one of the two matrixmaterials is a material having hole-transporting properties and theother matrix material is a material having electron-transportingproperties. The desired electron-transporting and hole-transportingproperties of the mixed matrix components may, however, also be combinedmainly or entirely in a single mixed matrix component, in which case thefurther mixed matrix component(s) fulfil(s) other functions. The twodifferent matrix materials may be present in a ratio of 1:50 to 1:1,preferably 1:20 to 1:1, more preferably 1:10 to 1:1 and most preferably1:4 to 1:1.

There follows a disclosure of the material classes that are used withpreference in the functional layers in question in the device.

Preferred phosphorescent emitters for use in the emitting layer can befound in the applications WO 00/70655, WO 01/41512, WO 02/02714, WO02/15645, EP 1191613, EP 1191612, EP 1191614, WO 05/033244, WO 05/019373and US 2005/0258742. In general, all phosphorescent complexes as usedfor phosphorescent OLEDs according to the prior art and as known tothose skilled in the art in the field of organic electroluminescentdevices are suitable.

Preferred fluorescent emitters are selected from the class of thearylamines. An arylamine or an aromatic amine in the context of thisinvention is understood here to mean a compound containing threesubstituted or unsubstituted aromatic or heteroaromatic ring systemsbonded directly to the nitrogen. Preferably, at least one of thesearomatic or heteroaromatic ring systems is a fused ring system, morepreferably having at least 14 aromatic ring atoms. Preferred examples ofthese are aromatic anthraceneamines, aromatic anthracenediamines,aromatic pyreneamines, aromatic pyrenediamines, aromatic chryseneaminesor aromatic chrysenediamines. An aromatic anthraceneamine is understoodto mean a compound in which a diarylamino group is bonded directly to ananthracene group, preferably in the 9 position. An aromaticanthracenediamine is understood to mean a compound in which twodiarylamino groups are bonded directly to an anthracene group,preferably in the 9,10 positions. Aromatic pyreneamines, pyrenediamines,chryseneamines and chrysenediamines are defined analogously, where thediarylamino groups are bonded to the pyrene preferably in the 1 positionor 1,6 positions. Further preferred emitting compounds areindenofluorenamines or -diamines, for example according to WO2006/108497 or WO 2006/122630, benzoindenofluoreneamines or -diamines,for example according to WO 2008/006449, and dibenzoindenofluoreneaminesor -diamines, for example according to WO 2007/140847, and theindenofluorene derivatives having fused aryl groups disclosed in WO2010/012328. Likewise preferred are the pyrenearylamines disclosed in WO2012/048780 and in WO 2013/185871. Likewise preferred are thebenzoindenofluoreneamines disclosed in WO 2014/037077, thebenzofluoreneamines disclosed in WO 2014/106522, the extendedbenzoindenofluorenes disclosed in WO 2014/111269 and in WO 2017/036574,the phenoxazines disclosed in WO 2017/028940 and WO 2017/028941, and thefluorene derivatives bonded to furan units or to thiophene units thatare disclosed in WO 2016/150544.

Useful matrix materials, preferably for fluorescent emitting layers,include materials of various substance classes. Preferred matrixmaterials are selected from the classes of the oligoarylenes (e.g.2,2′,7,7′-tetraphenyispirobifluorene according to EP 676461 ordinaphthylanthracene), especially of the oligoarylenes containing fusedaromatic groups, the oligoarylenevinylenes (e.g. DPVBi or spiro-DPVBiaccording to EP 676461), the polypodal metal complexes (for exampleaccording to WO 2004/081017), the hole-conducting compounds (for exampleaccording to WO 2004/058911), the electron-conducting compounds,especially ketones, phosphine oxides, sulfoxides, etc. (for exampleaccording to WO 2005/084081 and WO 2005/084082), the atropisomers (forexample according to WO 2006/048268), the boronic acid derivatives (forexample according to WO 2006/117052) or the benzanthracenes (for exampleaccording to WO 2008/145239). Particularly preferred matrix materialsare selected from the classes of the oligoarylenes comprisingnaphthalene, anthracene, benzanthracene and/or pyrene or atropisomers ofthese compounds, the oligoarylenevinylenes, the ketones, the phosphineoxides and the sulfoxides. Very particularly preferred matrix materialsare selected from the classes of the oligoarylenes comprisinganthracene, benzanthracene, benzophenanthrene and/or pyrene oratropisomers of these compounds. An oligoarylene in the context of thisinvention shall be understood to mean a compound in which at least threearyl or arylene groups are bonded to one another. Preference is furthergiven to the anthracene derivatives disclosed in WO 2006/097208, WO2006/131192, WO 2007/065550, WO 2007/110129, WO 2007/065678, WO2008/145239, WO 2009/100925, WO 2011/054442 and EP 1553154, the pyrenecompounds disclosed in EP 1749809, EP 1905754 and US 2012/0187826, thebenzanthracenylanthracene compounds disclosed in WO 2015/158409, theindenobenzofurans disclosed in WO 2017/025165, and thephenanthrylanthracenes disclosed in WO 2017/036573.

Preferred matrix materials for phosphorescent emitting compounds arearomatic ketones, aromatic phosphine oxides or aromatic sulfoxides andsulfones, for example according to WO 2004/013080, WO 2004/093207, WO2006/005627 or WO 2010/006680, triarylamines, carbazole derivatives,e.g. CBP (N,N-biscarbazolylbiphenyl) or the carbazole derivativesdisclosed in WO 2005/039246, US 2005/0069729, JP 2004/288381, EP 1205527or WO 2008/086851, indolocarbazole derivatives, for example according toWO 2007/063754 or WO 2008/056746, indenocarbazole derivatives, forexample according to WO 2010/136109, WO 2011/000455 or WO 2013/041176,azacarbazole derivatives, for example according to EP 1617710, EP1617711, EP 1731584, JP 2005/347160, bipolar matrix materials, forexample according to WO 2007/137725, silanes, for example according toWO 2005/111172, azaboroles or boronic esters, for example according toWO 2006/117052, triazine derivatives, for example according to WO2010/015306, WO 2007/063754 or WO 2008/056746, zinc complexes, forexample according to EP 652273 or WO 2009/062578, diazasilole ortetraazasilole derivatives, for example according to WO 2010/054729,diazaphosphole derivatives, for example according to WO 2010/054730,bridged carbazole derivatives, for example according to US 2009/0136779,WO 2010/050778, WO 2011/042107, WO 2011/088877 or WO 2012/143080,triphenylene derivatives, for example according to WO 2012/048781, orlactams, for example according to WO 2011/116865 or WO 2011/137951.

Further compounds which are used alongside the compounds of the formula(I), preferably in hole-transporting layers of the OLEDs of theinvention, are especially indenofluoreneamine derivatives (for exampleaccording to WO 06/122630 or WO 06/100896), the amine derivativesdisclosed in EP 1661888, hexaazatriphenylene derivatives (for exampleaccording to WO 01/049806), amine derivatives with fused aromatics (forexample according to U.S. Pat. No. 5,061,569), the amine derivativesdisclosed in WO 95/09147, monobenzoindenofluoreneamines (for exampleaccording to WO 08/006449), dibenzoindenofluoreneamines (for exampleaccording to WO 07/140847), spirobifluoreneamines (for example accordingto WO 2012/034627 or WO 2013/120577), fluoreneamines (for exampleaccording to WO 2014/015937, WO 2014/015938, WO 2014/015935 and WO2015/082056), spirodibenzopyranamines (for example according to WO2013/083216), dihydroacridine derivatives (for example according to WO2012/150001), spirodibenzofurans and spirodibenzothiophenes, for exampleaccording to WO 2015/022051 and WO 2016/102048 and WO 2016/131521,phenanthrenediarylamines, for example according to WO 2015/131976,spirotribenzotropolones, for example according to WO 2016/087017,spirobifluorenes with meta-phenyldiamine groups, for example accordingto WO 2016/078738, spirobisacridines, for example according to WO2015/158411, xanthenediarylamines, for example according to WO2014/072017, and 9,10-dihydroanthracene spiro compounds with diarylaminogroups according to WO 2015/086108.

Materials used for the electron transport layer may be any materials asused according to the prior art as electron transport materials in theelectron transport layer. Especially suitable are aluminium complexes,for example Alq₃, zirconium complexes, for example Zrq₄, lithiumcomplexes, for example Liq, benzimidazole derivatives, triazinederivatives, pyrimidine derivatives, pyridine derivatives, pyrazinederivatives, quinoxaline derivatives, quinoline derivatives, oxadiazolederivatives, aromatic ketones, lactams, boranes, diazaphospholederivatives and phosphine oxide derivatives. Further suitable materialsare derivatives of the abovementioned compounds as disclosed in JP2000/053957, WO 2003/060956, WO 2004/028217, WO 2004/080975 and WO2010/072300.

Preferred cathodes of the electronic device are metals having a low workfunction, metal alloys or multilayer structures composed of variousmetals, for example alkaline earth metals, alkali metals, main groupmetals or lanthanoids (e.g. Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.).Additionally suitable are alloys composed of an alkali metal or alkalineearth metal and silver, for example an alloy composed of magnesium andsilver. In the case of multilayer structures, in addition to the metalsmentioned, it is also possible to use further metals having a relativelyhigh work function, for example Ag or Al, in which case combinations ofthe metals such as Ca/Ag, Mg/Ag or Ba/Ag, for example, are generallyused. It may also be preferable to introduce a thin interlayer of amaterial having a high dielectric constant between a metallic cathodeand the organic semiconductor. Examples of useful materials for thispurpose are alkali metal or alkaline earth metal fluorides, but also thecorresponding oxides or carbonates (e.g. LiF, Li₂O, BaF₂, MgO, NaF, CsF,Cs₂CO₃, etc.). It is also possible to use lithium quinolinate (LiQ) forthis purpose. The layer thickness of this layer is preferably between0.5 and 5 nm.

Preferred anodes are materials having a high work function. Preferably,the anode has a work function of greater than 4.5 eV versus vacuum.Firstly, metals having a high redox potential are suitable for thispurpose, for example Ag, Pt or Au. Secondly, metal/metal oxideelectrodes (e.g. Al/Ni/NiOx, Al/PtOx) may also be preferred. For someapplications, at least one of the electrodes has to be transparent orpartly transparent in order to enable the irradiation of the organicmaterial (organic solar cell) or the emission of light (OLED, O-laser).Preferred anode materials here are conductive mixed metal oxides.Particular preference is given to indium tin oxide (ITO) or indium zincoxide (IZO). Preference is further given to conductive doped organicmaterials, especially conductive doped polymers. In addition, the anodemay also consist of two or more layers, for example of an inner layer ofITO and an outer layer of a metal oxide, preferably tungsten oxide,molybdenum oxide or vanadium oxide.

The device is structured (according to the application),contact-connected and finally sealed, in order to rule out damagingeffects by water and air.

In a preferred embodiment, the electronic device is characterized inthat one or more layers are coated by a sublimation process. In thiscase, the materials are applied by vapour deposition in vacuumsublimation systems at an initial pressure of less than 10⁻⁵ mbar,preferably less than 10⁻⁶ mbar. In this case, however, it is alsopossible that the initial pressure is even lower, for example less than10⁻⁷ mbar.

Preference is likewise given to an electronic device, characterized inthat one or more layers are coated by the OVPD (organic vapour phasedeposition) method or with the aid of a carrier gas sublimation. In thiscase, the materials are applied at a pressure between 10⁻⁵ mbar and 1bar. A special case of this method is the OVJP (organic vapour jetprinting) method, in which the materials are applied directly by anozzle and thus structured.

Preference is additionally given to an electronic device, characterizedin that one or more layers are produced from solution, for example byspin-coating, or by any printing method, for example screen printing,flexographic printing, nozzle printing or offset printing, but morepreferably LITI (light-induced thermal imaging, thermal transferprinting) or inkjet printing. For this purpose, soluble compounds offormula (I) are needed. High solubility can be achieved by suitablesubstitution of the compounds.

It is further preferable that an electronic device of the invention isproduced by applying one or more layers from solution and one or morelayers by a sublimation method.

According to the invention, the electronic devices can be used indisplays, as light sources in lighting applications and as light sourcesin medical and/or cosmetic applications (for example light therapy).

The invention further provides a compound as such that corresponds to aformula (S)

where an A group has to be bonded to at least one group selected fromthe B₁ and B₂ groups, and where the variables that occur are as follows:

-   B₁, B₂ are the same or different at each instance and are N or CR²    or C, where a B₁ or B₂ group is C in the specific case when an A    group is bonded to it;-   Z is the same or different at each instance and is CR² or N or C,    where a Z group is C in the specific case when an E group is bonded    to the Z group in question;-   A is an arylamino group optionally substituted by one or more R¹    radicals, or a carbazole-containing group optionally substituted by    one or more R¹ radicals;-   E is a single bond;-   X is O or S;-   R¹ is the same or different at each instance and is selected from H,    D, F, C(═O)R³, CN, Si(R³)₃, N(R³)₂, P(═O)(R³)₂, OR³, S(═O)R³,    S(═O)₂R³, straight-chain alkyl or alkoxy groups having 1 to 20    carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to    20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon    atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and    heteroaromatic ring systems having 5 to 40 aromatic ring atoms;    where two or more R¹ radicals may be joined to one another and may    form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups    mentioned and the aromatic ring systems and heteroaromatic ring    systems mentioned may each be substituted by one or more R³    radicals; and where one or more CH₂ groups in the alkyl, alkoxy,    alkenyl and alkynyl groups mentioned may be replaced    -   by —R³C═CR³—, —C≡C—, Si(R³)₂, C═O, C═NR³, —C(═O)O—, C(═O)NR³—,        NR³, P(═O)(R³), —O—, —S—, SO or SO₂;-   R² is the same or different at each instance and is selected from H,    D, F, C(═O)R³, CN, Si(R³)₃, N(R³)₂, P(═O)(R³)₂, OR³, S(═O)R³,    S(═O)₂R³, straight-chain alkyl or alkoxy groups having 1 to 20    carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to    20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon    atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and    heteroaromatic ring systems having 5 to 40 aromatic ring atoms;    where two or more R² radicals may be joined to one another and may    form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups    mentioned and the aromatic ring systems and heteroaromatic ring    systems mentioned may each be substituted by one or more R³    radicals; and where one or more CH₂ groups in the alkyl, alkoxy,    alkenyl and alkynyl groups mentioned may be replaced    -   by —R³C═CR³—, —C≡C—, Si(R³)₂, C═O, C═NR³, —C(═O)O—, C(═O)NR³—,        NR³, P(═O)(R³), —O—, —S—, SO or SO₂;-   R³ is the same or different at each instance and is selected from H,    D, F, C(═O)R⁴, CN, Si(R⁴)₃, N(R⁴)₂, P(═O)(R⁴)₂, OR⁴, S(═O)R⁴,    S(═O)₂R⁴, straight-chain alkyl or alkoxy groups having 1 to 20    carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to    20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon    atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and    heteroaromatic ring systems having 5 to 40 aromatic ring atoms;    where two or more R³ radicals may be joined to one another and may    form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups    mentioned and the aromatic ring systems and heteroaromatic ring    systems mentioned may each be substituted by one or more R⁴    radicals; and where one or more CH₂ groups in the alkyl, alkoxy,    alkenyl and alkynyl groups mentioned may be replaced    -   by —R⁴C═CR⁴—, —C≡C—, Si(R⁴)₂, C═O, C═NR⁴, —C(═O)O—, C(═O)NR⁴—,        NR⁴, P(═O)(R⁴), —O—, —S—, SO or SO₂;-   R⁴ is the same or different at each instance and is selected from H,    D, F, CN, alkyl or alkoxy groups having 1 to 20 carbon atoms,    alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring    systems having 6 to 40 aromatic ring atoms and heteroaromatic ring    systems having 5 to 40 aromatic ring atoms; where two or more R⁴    radicals may be joined to one another and may form a ring; and where    the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems    and heteroaromatic ring systems mentioned may be substituted by F or    CN;-   i is 0 or 1.

The terms “arylamino group” and “carbazole group” as A group areunderstood here to mean groups as defined above.

In the compound of the formula (S), X is preferably O.

In addition, i is preferably 1.

In addition, preferably not more than 2 Z groups per ring are N. Furtherpreferably, not more than 4 Z groups per compound of the formula (S),most preferably not more than 2 Z groups per compound of the formula(S), are Z.

More preferably, Z is CR², where, in the case that an E group is bondedto the Z group in question, this Z group is C.

Preferably, an A group is bonded to exactly one of the two B₁ and B₂groups, and no A group is bonded to the other of the two B₁ and B₂groups.

With regard to the variables R¹ to R³, the preferred embodimentsspecified above are applicable.

Preferably, the A group is an arylamino group optionally substituted byone or more R¹ radicals. The A group as arylamino group is preferablydefined as specified above and preferably corresponds to the formula (A)as specified above.

Preferred embodiments of the compound of the formula (S) correspond tothe formulae (S-1) and (S-2)

where the variables that occur are as defined above.

Particular preference is given to compounds of the formula (S-1).

A particularly preferred embodiment of the compounds of the formula (S)is that of compounds of the formula (S-1-1)

where the compounds may each be substituted on the benzene rings at thepositions shown as unsubstituted by R² radicals, and where the variablesthat occur as follows:

-   L¹ is the same or different at each instance and is C—O, Si(R¹)₂,    PR¹, P(═O)(R¹), O, S, SO, SO₂, an alkylene group having 1 to 20    carbon atoms or an alkenylene or alkynylene group having 2 to 20    carbon atoms, where one or more CH₂ groups in the groups mentioned    may be replaced by C═O, C═NR¹, C═O—O, C═O—NR¹, Si(R¹)₂, NR¹,    P(═O)(R¹), O, S, SO or SO₂ and where one or more hydrogen atoms in    the abovementioned groups may be replaced by D, F or CN, or an    aromatic or heteroaromatic ring system which has 6 to 24 aromatic    ring atoms and may be substituted by one or more R¹ radicals;-   Ar¹ is the same or different at each instance and is an aromatic or    heteroaromatic ring system which has 6 to 30 aromatic ring atoms and    may be substituted by one or more R¹ radicals;-   k is 0, 1, 2 or 3;-   R¹, R², R³ and R⁴ are as defined above.

Preferably, the compounds of the formula (S-1-1) are unsubstituted onthe benzene rings at the positions shown as unsubstituted.

Preferred embodiments of the formula (S) are the compounds listed in thetable above under the base skeletons (I-1-5-O) and (I-1-5-S).

Preferred compounds of the formula (S) are depicted below:

The compounds of the formula (S) can be prepared by means of customarymethods of synthetic organic chemistry. Use is made here particularly ofBuchwald and Suzuki reactions, nucleophilic addition reactions ontocarbonyl groups, and ring-closure reactions by electrophilic aromaticsubstitution.

A preferred process for preparing compounds of the formula (S) proceedsas follows: First of all, a metallated ether or thioether compound (B inScheme 1 below) is added onto a ketone C, followed by a ring-closurereaction. Subsequently, an amino group or an aryl group containing anamino group is inserted via a Buchwald or Suzuki reaction. Themetallated ether or thioether compound is preferably a lithiatedcompound or a corresponding Grignard compound.

Alternatively, the addition of the metallated ether or thioether grouponto the ketone and the ring-closure reaction can also take place aftera Suzuki or Buchwald coupling, as shown in Scheme 2.

The application thus provides a process for preparing a compound of theformula (S), characterized in that it comprises an addition of ametallated ether or thioether compound onto a diaryl ketone and asubsequent ring-closure reaction. The metallated ether or thioethercompound is preferably a metallated diaryl ether or diaryl thioethercompound, most preferably a lithiated diaryl ether or diaryl thioethercompound or a corresponding Grignard derivative of the diaryl ether ordiaryl thioether compound.

The above-described compounds, especially compounds substituted byreactive leaving groups, such as bromine, iodine, chlorine, boronic acidor boronic ester, may find use as monomers for production ofcorresponding oligomers, dendrimers or polymers. Suitable reactiveleaving groups are, for example, bromine, iodine, chlorine, boronicacids, boronic esters, amines, alkenyl or alkynyl groups having aterminal C—C double bond or C—C triple bond, oxiranes, oxetanes, groupswhich enter into a cydoaddition, for example a 1,3-dipolarcycloaddition, for example dienes or azides, carboxylic acidderivatives, alcohols and silanes.

The invention therefore further provides oligomers, polymers ordendrimers containing one or more compounds of formula (S), wherein thebond(s) to the polymer, oligomer or dendrimer may be localized at anydesired positions substituted by R¹ or R² in formula (S). According tothe linkage of the compound of formula (S), the compound is part of aside chain of the oligomer or polymer or part of the main chain. Anoligomer in the context of this invention is understood to mean acompound formed from at least three monomer units. A polymer in thecontext of the invention is understood to mean a compound formed from atleast ten monomer units. The polymers, oligomers or dendrimers of theinvention may be conjugated, partly conjugated or nonconjugated. Theoligomers or polymers of the invention may be linear, branched ordendritic. In the structures having linear linkage, the units of formula(S) may be joined directly to one another, or they may be joined to oneanother via a bivalent group, for example via a substituted orunsubstituted alkylene group, via a heteroatom or via a bivalentaromatic or heteroaromatic group. In branched and dendritic structures,it is possible, for example, for three or more units of formula (S) tobe joined via a trivalent or higher-valency group, for example via atrivalent or higher-valency aromatic or heteroaromatic group, to give abranched or dendritic oligomer or polymer.

For the repeat units of formula (S) in oligomers, dendrimers andpolymers, the same preferences apply as described above for compounds offormula (S).

For preparation of the oligomers or polymers, the monomers of theinvention are homopolymerized or copolymerized with further monomers.Suitable and preferred comonomers are chosen from fluorenes (for exampleaccording to EP 842208 or WO 2000/22026), spirobifluorenes (for exampleaccording to EP 707020, EP 894107 or WO 2006/061181), paraphenylenes(for example according to WO 1992/18552), carbazoles (for exampleaccording to WO 2004/070772 or WO 2004/113468), thiophenes (for exampleaccording to EP 1028136), dihydrophenanthrenes (for example according toWO 2005/014689 or WO 2007/006383), cis- and trans-indenofluorenes (forexample according to WO 2004/041901 or WO 2004/113412), ketones (forexample according to WO 2005/040302), phenanthrenes (for exampleaccording to WO 2005/104264 or WO 2007/017066) or else a plurality ofthese units. The polymers, oligomers and dendrimers typically containstill further units, for example emitting (fluorescent orphosphorescent) units, for example vinyltriarylamines (for exampleaccording to WO 2007/068325) or phosphorescent metal complexes (forexample according to WO 2006/003000), and/or charge transport units,especially those based on triarylamines.

The polymers and oligomers of the invention are generally prepared bypolymerization of one or more monomer types, of which at least onemonomer leads to repeat units of the formula (S) in the polymer.Suitable polymerization reactions are known to those skilled in the artand are described in the literature. Particularly suitable and preferredpolymerization reactions which lead to formation of C—C or C—N bonds arethe Suzuki polymerization, the Yamamoto polymerization, the Stillepolymerization and the Hartwig-Buchwald polymerization.

For the processing of the compounds of the invention from a liquidphase, for example by spin-coating or by printing methods, formulationsof the compounds of the invention are required. These formulations may,for example, be solutions, dispersions or emulsions. For this purpose,it may be preferable to use mixtures of two or more solvents. Suitableand preferred solvents are, for example, toluene, anisole, o-, m- orp-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF,methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially3-phenoxytoluene, (−)-fenchone, 1,2,3,5-tetramethylbenzene,1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole,2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole,3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpineol,benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone,cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane,methyl benzoate, NMP, p-cymene, phenetole, 1,4-diisopropylbenzene,dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycolbutyl methyl ether, diethylene glycol dibutyl ether, triethylene glycoldimethyl ether, diethylene glycol monobutyl ether, tripropylene glycoldimethyl ether, tetraethylene glycol dimethyl ether,2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene,octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane or mixtures of thesesolvents.

The invention therefore further provides a formulation, especially asolution, dispersion or emulsion, comprising at least one compound offormula (S) and at least one solvent, preferably an organic solvent. Theway in which such solutions can be prepared is known to those skilled inthe art and is described, for example, in WO 2002/072714, WO 2003/019694and the literature cited therein.

The compounds of the invention are suitable for use in electronicdevices, especially in organic electroluminescent devices (OLEDs).Depending on the substitution, the compounds are used in differentfunctions and layers.

In this regard, the same preferred embodiments as described above forthe compounds of the formula (I) are applicable. In addition, thecompounds of the formula (S) are also particularly suitable for use inan electron blocker layer of an OLED.

WORKING EXAMPLES A) Synthesis Examples Example 1-1

Synthesis of the Inventive Compound 1-1 and Variants

Intermediate I-1

26.8 g of phenyl(9,9-dimethyl-9H-fluoren-2-yl)amine (87.6 mmol) and 25 gof iodobenzofluorenone (87.6 mmol) are dissolved in 700 ml of toluene.The solution is degassed and saturated with N₂. Thereafter, 3.5 ml (3.5mmol) of a 1 M tri-tert-butylphosphine solution and 0.46 g (1.75 mmol)of palladium(II) acetate are added thereto, and then 16.8 g of sodiumtert-butoxide (175 mmol) are added. The reaction mixture is heated toboiling under a protective atmosphere for 5 h. The mixture issubsequently partitioned between toluene and water, and the organicphase is washed three times with water and dried over Na₂SO₄ andconcentrated by rotary evaporation. After the crude product has beenfiltered through silica gel with toluene, the remaining residue isrecrystallized from heptane/toluene. The yield is 33 g (81% of theory).

The following compounds are prepared in an analogous manner:

Reactant 1 Reactant 2 Product Yield I-2

85% I-3

71% I-4

82% I-5

72% I-6

74% I-7

74% I-8

62% I-9

35% I-10

70% I-11

67%

Compound 1-1

17.37 g (69.6 mmol) of 1-bromo-2-diphenyl ether are dissolved in abaked-out flask in 300 ml of dried THF. The reaction mixture is cooledto −78° C. At this temperature, 30 ml of a 2.5 M solution of n-BuLi inhexane (69.7 mmol) are slowly added dropwise. The mixture is stirred at−70° C. for a further 1 hour. Subsequently, 30 g of the bromofluorenonederivative (63 mmol) are dissolved in 200 ml of THF and added dropwiseat −70° C. After the addition has ended, the reaction mixture is warmedgradually to room temperature, quenched with NH₄Cl and then concentratedon a rotary evaporator.

300 ml of acetic acid are added cautiously to the concentrated solutionand then 20 ml of fuming HCl are added. The mixture is heated to 75° C.and kept there for 6 hours. During this time, a white solid precipitatesout. The mixture is then cooled to room temperature, and theprecipitated solids are filtered off with suction and washed with waterand methanol. Yield: 35 g (88%)

The solids are recrystallized from heptane/toluene and finally sublimedunder high vacuum.

The following compounds are prepared in an analogous manner:

Reactant 1 Reactant 2 Product Yield 1-2

70% 1-3

77% 1-5

65% 1-6

69% 1-7

79% 1-8

81% 1-9

80% 1-10

40% 1-11

79%

Example 2-1

Synthesis of the Inventive Compound 2-1 and Variants

Intermediate II-1

38 g of 4-chlorophenylboronic acid (243 mmol) and 60 g of1-bromofluoren-9-one (232 mmol) are suspended in 800 ml of THF. 230 mlof 2 M potassium carbonate solution are slowly added dropwise. Thesolution is degassed and saturated with N₂. Thereafter, 8 g (7 mmol) ofPd(Ph₃P)₄ are added. The reaction mixture is heated to boiling under aprotective atmosphere for 16 h. The mixture is subsequently partitionedbetween toluene and water, and the organic phase is washed three timeswith water and dried over Na₂SO₄ and concentrated by rotary evaporation.After the crude product has been filtered through silica gel withtoluene, the remaining residue is recrystallized from MeOH. The yield is63 g (90% of theory).

The following compounds are prepared in an analogous manner:

Reactant 1 Reactant 2 Product Yield II-2

80% II-3

88% II-4

82% II-5

89% II-6

64% II-7

80% II-8

83%

Intermediate III-1

30 g (120 mmol) of 1-bromo-2-diphenyl ether are dissolved in a baked-outflask in 500 ml of dried THF. The reaction mixture is cooled to −78° C.At this temperature, 480 ml of a 2.5 M solution of n-BuLi in hexane (120mmol) are slowly added dropwise. The mixture is stirred at −70° C. for afurther 1 hour. Subsequently, 33 g of 1-(4-chlorophenyl)fluorenone (114mmol) are dissolved in 100 ml of THF and added dropwise at −70° C. Afterthe addition has ended, the reaction mixture is warmed gradually to roomtemperature, quenched with NH₄Cl and then concentrated on a rotaryevaporator.

300 ml of acetic acid are added cautiously to the concentrated solutionand then 20 ml of fuming HCl are added. The mixture is heated to 75° C.and kept there for 6 hours. During this time, a white solid precipitatesout. The mixture is then cooled to room temperature, and theprecipitated solids are filtered off with suction and washed with waterand methanol. Yield: 38 g (70%).

Finally, the residue is recrystallized.

The following compounds are prepared in an analogous manner:

Reactant 1 Reactant 2 Product Yield III-2

70% III-3

77% III-4

67% III-5

65% III-6

73% III-7

69% III-8

83% III-9

71%

Compound 2-1

16.3 g of biphenyl-3-yl(9,9-dimethyl-9H-fluoren-2-yl)amine (45.26 mmol)and 29 g of the chloro derivative III-1 (45.2 mmol) are dissolved in 400ml of toluene. The solution is degassed and saturated with N₂.Thereafter, 740 mg (1.81 mmol) of S-Phos and 830 mg (0.9 mmol) ofPd₂(dba)₃ are added thereto, and then 6.5 g of sodium tert-butoxide(67.7 mmol) are added. The reaction mixture is heated to boiling under aprotective atmosphere for 5 h. The mixture is subsequently partitionedbetween toluene and water, and the organic phase is washed three timeswith water and dried over Na₂SO₄ and concentrated by rotary evaporation.After the crude product has been filtered through silica gel withtoluene, the remaining residue is recrystallized from heptane/toluene.The yield is 27 g (78% of theory). The solids are recrystallized fromheptane/toluene and finally sublimed under high vacuum.

The following compounds are prepared in an analogous manner:

Reactant 1 Reactant 2 Product Yield 2-2

78% 2-3

71% 2-4

82% 2-5

89% 2-6

69% 2-7

88% 2-8

85% 2-9

75% 2-10

75%

B) Use Examples

OLED devices according to the present application and comparativedevices are produced in order to show the technical effects of the OLEDdevices of the invention. The OLEDs are produced according to thegeneral method described in the working examples of publishedspecification WO 2004/058911, unless stated otherwise below.

The OLEDs produced have glass plaques coated with structured ITO (indiumtin oxide) in a thickness of 50 nm as substrates. The layers that followthe substrate, the thickness thereof and the substances of which theyconsist are listed separately for each example device in one of thetables which follow. The counterelectrode applied as the last layer isan aluminium layer in a thickness of 100 nm.

All materials are applied by thermal gas phase deposition in a vacuumchamber. In the examples, the emission layer always consists of at leastone matrix material and an emitting compound as dopant. The latter isadded to the matrix material(s) by coevaporation. An expression “SMB:SEB(5%)” means here that the material SMB is present in the layer in aproportion of 95% by volume, and the material SEB is present in thelayer in a proportion of 5% by volume. Not just the emission layer butalso other layers may analogously consist of a mixture of two or morematerials.

The OLEDs are characterized by standard methods. For this purpose, theelectroluminescence spectra, the external quantum efficiency (EQE,measured in %) as a function of luminance, calculated fromcurrent-voltage-luminance characteristics (IUL characteristics) assumingLambertian emission characteristics, and the lifetime are determined. Inthat case, the expression “EQE @ 40 mA/cm²” means, for example, theexternal quantum efficiency at an operating luminance of 40 mA/cm². Thelifetime is measured at 20 mA/cm² for green-emitting devices, and at 60mA/cm² for blue-emitting devices. Assuming an exponential drop in theOLEDs, the LT80 values for the lifetime are then approximated with anacceleration factor of 1.8 to the lifetime at 1000 cd/m². LT80 @ 1000cd/m² is then the approximated lifetime by which the OLED has droppedfrom a starting luminance of 1000 cd/m² to a luminance of 800 cd/m².

The chemical structures of the materials that are used in the examplesare given in Table A. The synthesis of the spiroxantheneamines iseffected as in the preceding Synthesis Examples section, or it can beeffected as in the prior art, for example as disclosed in WO2014/072017.

TABLE A

1) Use of Spiroxantheneamines as HTL and HIL Materials

The following OLEDs C3 (comparative example) and I3, I5, I7, I9, I10,I14, I15 and I16 (inventive examples) are produced.

C3 as a comparative example comprises the compound HIM (aspirobifluorene derivative) as HTL and HIL material. The abovementioneduse examples I3, I5, I7, I9, I10, I14, I15 and I16 comprise thematerials HTM2, HTM4, HTM5, HTM6, HTM7, HTM8, HTM9, HTM13, HTM14 andHTM15 as HTL and HIL materials. Otherwise, the construction thereof isidentical to that of C3 (Table 1).

For all the devices of the invention, a significant rise in lifetime isobserved compared to example C3 (Table 2).

This shows the excellent suitability of the spiroxantheneamines as HILand HTL materials, compared to the HTL/HIL material HIM according to theprior art.

TABLE 1 Structure of the OLEDs HIL HTL EBL EML ETL EIL Thick- Thick-Thick- Thick- Thick- Thick- ness/ ness/ ness/ ness/ ness/ ness/ Ex. nmnm nm nm nm nm C3 HIM: HIM HTMC2 SMB: ETM: LiQ F4TCNQ(5%) 180 nm 10 nmSEB(5%) LiQ(50%) 1 nm 20 nm 20 nm 30 nm I3 HTM2: HTM2 HTMC2 SMB: ETM:LiQ F4TCNQ(5%) 180 nm 10 nm SEB(5%) LiQ(50%) 1 nm 20 nm 20 nm 30 nm I5HTM4: HTM4 HTMC2 SMB: ETM: LiQ F4TCNQ(5%) 180 nm 10 nm SEB(5%) LiQ(50%)1 nm 20 nm 20 nm 30 nm I7 HTM6: HTM6 HTMC2 SMB: ETM: LiQ F4TCNQ(5%) 180nm 10 nm SEB(5%) LiQ(50%) 1 nm 20 nm 20 nm 30 nm I9 HTM8: HTM8 HTMC2SMB: ETM: LiQ F4TCNQ(5%) 180 nm 10 nm SEB(5%) LiQ(50%) 1 nm 20 nm 20 nm30 nm I10 HTM9: HTM9 HTMC2 SMB: ETM: LiQ F4TCNQ(5%) 180 nm 10 nm SEB(5%)LiQ(50%) 1 nm 20 nm 20 nm 30 nm I14 HTM5: HTM13 HTMC2 SMB: ETM: LiQF4TCNQ(5%) 180 nm 10 nm SEB(5%) LiQ(50%) 1 nm 20 nm 20 nm 30 nm I15HTM6: HTM14 HTMC2 SMB: ETM: LiQ F4TCNQ(5%) 180 nm 10 nm SEB(5%) LiQ(50%)1 nm 20 nm 20 nm 30 nm I16 HTM7: HTM15 HTMC2 SMB: ETM: LiQ F4TCNQ(5%)180 nm 10 nm SEB(5%) LiQ(50%) 1 nm 20 nm 20 nm 30 nm

TABLE 2 Data of the OLEDs U LT80 @ 10 mA/cm² @ 1000 cd/m² Ex. [V] [h] C33.8 4790 I3 4.4 6800 I5 4.3 4960 I7 3.8 5610 I9 4.3 5180 I10 4.2 7390I14 3.9 5500 I15 3.8 6600 I16 4.0 7400

A comparison between OLEDs that differ merely by the fact that thespiroxantheneamines are present in the EBL rather than in the HTL/HIL isshown in Tables 3 and 4 below.

Table 3 shows the construction of the comparative OLEDs.

Table 4 shows the results of the direct comparisons with respect to oneanother. One line lists the data to be compared with one another in eachcase. In all cases, if the spiroxanthenes are present in the HIL/HTL,significantly higher lifetimes are obtained (examples on the right-handside of Table 4).

This shows the advantages that are obtained through the use of thespiroxantheneamine compounds in the HIL and the HTL of OLEDs.

TABLE 3 Structure of the OLEDs HIL HTL EBL EML ETL EIL Thick- Thick-Thick- Thick- Thick- Thick- ness/ ness/ ness/ ness/ ness/ ness/ Ex. nmnm nm nm nm nm I17 HIM: HIM HTM2 SMB: ETM: LiQ F4TCNQ(5%) 180 nm 10 nmSEB(5%) LiQ(50%) 1 nm 20 nm 20 nm 30 nm I19 HIM: HIM HTM4 SMB: ETM: LiQF4TCNQ(5%) 180 nm 10 nm SEB(5%) LiQ(50%) 1 nm 20 nm 20 nm 30 nm I21 HIM:HIM HTM6 SMB: ETM: LiQ F4TCNQ(5%) 180 nm 10 nm SEB(5%) LiQ(50%) 1 nm 20nm 20 nm 30 nm I23 HIM: HIM HTM8 SMB: ETM: LiQ F4TCNQ(5%) 180 nm 10 nmSEB(5%) LiQ(50%) 1 nm 20 nm 20 nm 30 nm I24 HIM: HIM HTM9 SMB: ETM: LiQF4TCNQ(5%) 180 nm 10 nm SEB(5%) LiQ(50%) 1 nm 20 nm 20 nm 30 nm

TABLE 4 Data of the OLEDs U @ 10 mA/ LT80 LT80 U cm² @ 1000 cd/m² @ 1000cd/m² @ 10 mA/cm² Ex. [V] [h] [h] [V] Ex. I17 3.9 3082 6800 4.4 E3 I193.8 2278 4960 4.3 E5 I21 3.9 2464 5610 3.8 E7 I23 3.7 3881 5180 4.3 E9I24 3.7 4126 7390 4.2 E10

2) Use of Spiroxanthenes Substituted by an Amino Group in the 1 Positionas EBL Materials

The following OLEDs C1, C2, I1 and I2 are produced (for construction seeTable 5).

C1 and C2 are comparative examples that use a 4-spirobifluoreneamine(HTMC2) as EBL material. C1 differs from C2 in that a differentspirobifluoreneamine is used as HIL and HTL material (HTMC1 in C1, andHTMC2 in C2).

I1 is a direct comparison with C1. In I1, the spiroxantheneamine HTM1 isused as EBL material in place of the spirobifluoreneamine HTMC2. I2 is adirect comparison with C2. In I2, the spiroxantheneamine HTM1 is used asEBL material in place of the spirobifluoreneamine HTMC2.

Both for I1 and for I2, a significant relative rise in lifetime (LT80)is observed compared to examples C1 and C2. In parallel, there is animprovement in the efficiency of the OLEDs (Table 6).

This shows the technical effect which is achieved with1-spiroxantheneamines, especially when used as EBL materials.

TABLE 5 Structure of the OLEDs HIL HTL EBL EML HBL ETL EIL Thick- Thick-Thick- Thick- Thick- Thick- Thick- ness/ ness/ ness/ ness/ ness/ ness/ness/ Ex. nm nm nm nm nm nm nm C1 HTMC1: HTMC1 HTMC2 H1:H2(29%): ETMETM: LiQ F4TCNQ(5%) 220 nm 10 nm TEG(12%) 10 nm LiQ(50%) 1 nm 20 nm 30nm 30 nm I1 HTMC1: HTMC1 HTM1 H1:H2(29%): ETM ETM: LiQ F4TCNQ(5%) 220 nm10 nm TEG(12%) 10 nm LiQ(50%) 1 nm 20 nm 30 nm 30 nm C2 HTMC2: HTMC2HTMC2 H1:H2(29%): ETM ETM: LiQ F4TCNQ(5%) 220 nm 10 nm TEG(12%) 10 nmLiQ(50%) 1 nm 20 nm 30 nm 30 nm I2 HTMC2: HTMC2 HTM1 H1:H2(29%): ETMETM: LiQ F4TCNQ(5%) 220 nm 10 nm TEG(12%) 10 nm LiQ(50%) 1 nm 20 nm 30nm 30 nm

TABLE 6 Data of the OLEDs U EQE LT80 @ 2 mA/cm² @ 2 mA/cm² @ 1000 cd/m²Ex. [V] % [h] C1 3.1 17.4 53400 I1 3.3 18.0 69900 C2 3.2 17.7 69000 I23.5 17.9 76400

1.-19. (canceled)
 20. An electronic device comprising, in this sequence,an anode, a hole-transporting layer, an emitting layer and a cathode,wherein said hole-transporting layer comprises a compound of a formula(I)

where: A is an arylamino group optionally substituted by one or more R¹radicals, or a carbazole-containing group optionally substituted by oneor more R¹ radicals; E is a single bond; X is O or S; Z is the same ordifferent at each instance and is CR² or N or C, where a Z group is C inthe specific case when an A or E group is bonded to the Z group inquestion; R¹ is the same or different at each instance and is selectedfrom H, D, F, C(═O)R³, CN, Si(R³)₃, N(R³)₂, P(═O)(R³)₂, OR³, S(═O)R³,S(═O)₂R³, straight-chain alkyl or alkoxy groups having 1 to 20 carbonatoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbonatoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromaticring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ringsystems having 5 to 40 aromatic ring atoms; where two or more R¹radicals may be joined to one another and may form a ring; where thealkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromaticring systems and heteroaromatic ring systems mentioned may each besubstituted by one or more R³ radicals; and where one or more CH₂ groupsin the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may bereplaced by —R³C═CR³—, —C≡C—, Si(R³)₂, C═O, C═NR³, —C(═O)O—, C(═O)NR³—,NR³, P(═O)(R³), —O—, —S—, SO or SO₂; R² is the same or different at eachinstance and is selected from H, D, F, C(═O)R³, CN, Si(R³)₃, N(R³)₂,P(═O)(R³)₂, OR³, S(═O)R³, S(═O)₂R³, straight-chain alkyl or alkoxygroups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxygroups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ringatoms, and heteroaromatic ring systems having 5 to 40 aromatic ringatoms; where two or more R² radicals may be joined to one another andmay form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groupsmentioned and the aromatic ring systems and heteroaromatic ring systemsmentioned may each be substituted by one or more R³ radicals; and whereone or more CH₂ groups in the alkyl, alkoxy, alkenyl and alkynyl groupsmentioned may be replaced by —R³C═CR³—, —C≡C—, Si(R³)₂, C═O, C═NR³,—C(═O)O—, C(═O)NR³—, NR³, P(═O)(R³), —O—, —S—, SO or SO₂; R³ is the sameor different at each instance and is selected from H, D, F, C(═O)R⁴, CN,Si(R⁴)₃, N(R⁴)₂, P(═O)(R⁴)₂, OR⁴, S(═O)R⁴, S(═O)₂R⁴, straight-chainalkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclicalkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynylgroups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40aromatic ring atoms, and heteroaromatic ring systems having 5 to 40aromatic ring atoms; where two or more R³ radicals may be joined to oneanother and may form a ring; where the alkyl, alkoxy, alkenyl andalkynyl groups mentioned and the aromatic ring systems andheteroaromatic ring systems mentioned may each be substituted by one ormore R⁴ radicals; and where one or more CH₂ groups in the alkyl, alkoxy,alkenyl and alkynyl groups mentioned may be replaced by —R⁴C═CR⁴—,—C≡C—, Si(R⁴)₂, C═O, C═NR⁴, —C(═O)O—, C(═O)NR⁴—, NR⁴, P(═O)(R⁴), —O—,—S—, SO or SO₂; R⁴ is the same or different at each instance and isselected from H, D, F, CN, alkyl or alkoxy groups having 1 to 20 carbonatoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromaticring systems having 6 to 40 aromatic ring atoms and heteroaromatic ringsystems having 5 to 40 aromatic ring atoms; where two or more R⁴radicals may be joined to one another and may form a ring; and where thealkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems andheteroaromatic ring systems mentioned may be substituted by F or CN; iis 0 or 1; n is the same or different at each instance and is 0 or 1,where the sum total of all the indices n is 1, 2, 3 or 4; where at leastone condition selected from conditions a) and b) is met: a) thehole-transporting layer directly adjoins the anode; b) there are atleast two further layers arranged between the hole-transporting layerand the emitting layer, and there are no further emitting layersarranged between the emitting layer and the anode.
 21. The electronicdevice according to claim 20, wherein X is O.
 22. The electronic deviceaccording to claim 20, wherein i is
 1. 23. The electronic deviceaccording to claim 20, wherein the sum total of the indices n is 1 or 2.24. The electronic device according to claim 20, wherein R¹ is the sameor different at each instance and is selected from H, F, CN,straight-chain alkyl groups having 1 to 20 carbon atoms, branched orcyclic alkyl groups having 3 to 20 carbon atoms, aromatic ring systemshaving 6 to 40 aromatic ring atoms, and heteroaromatic ring systemshaving 5 to 40 aromatic ring atoms, where the alkyl groups mentioned,the aromatic ring systems mentioned and the heteroaromatic ring systemsmentioned may each be substituted by one or more R³ radicals.
 25. Theelectronic device according to claim 20, wherein R² is the same ordifferent at each instance and is selected from H, F, CN, straight-chainalkyl groups having 1 to 20 carbon atoms, branched or cyclic alkylgroups having 3 to 20 carbon atoms, aromatic ring systems having 6 to 40aromatic ring atoms, and heteroaromatic ring systems having 5 to 40aromatic ring atoms, where the alkyl groups mentioned, the aromatic ringsystems mentioned and the heteroaromatic ring systems mentioned may eachbe substituted by one or more R³ radicals.
 26. The electronic deviceaccording to claim 20, wherein R³ is the same or different at eachinstance and is selected from H, F, CN, straight-chain alkyl groupshaving 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ringatoms, and heteroaromatic ring systems having 5 to 40 aromatic ringatoms, where the alkyl groups mentioned, the aromatic ring systemsmentioned and the heteroaromatic ring systems mentioned may each besubstituted by one or more R⁴ radicals.
 27. The electronic deviceaccording to claim 20, wherein the A group is an arylamino group whichmay be substituted by one or more R¹ radicals.
 28. The electronic deviceaccording to claim 20, wherein the arylamino group as A groupcorresponds to a formula (A)

where: L¹ is the same or different at each instance and is C═O, Si(R¹)₂,PR¹, P(═O)(R¹), O, S, SO, SO₂, an alkylene group having 1 to 20 carbonatoms or an alkenylene or alkynylene group having 2 to 20 carbon atoms,where one or more CH₂ groups in the groups mentioned may be replaced byC═O, C═NR¹, C═O—O, C═O—NR¹, Si(R¹)₂, NR¹, P(═O)(R¹), O, S, SO or SO₂ andwhere one or more hydrogen atoms in the abovementioned groups may bereplaced by D, F or CN, or an aromatic or heteroaromatic ring systemwhich has 6 to 24 aromatic ring atoms and may be substituted by one ormore R¹ radicals; Ar¹ is the same or different at each instance and isan aromatic or heteroaromatic ring system which has 6 to 30 aromaticring atoms and may be substituted by one or more R¹ radicals; Y isselected from a single bond, BR¹, C(R¹)₂, C(R¹)₂—C(R¹)₂, Si(R¹)₂,Si(R¹)₂—Si(R¹)₂, C═O, C═NR¹, C═C(R¹)₂, C(═O)N(R¹), O, S, S═O, SO₂ andNR¹; k is 0, 1, 2 or 3; m is 0 or 1; where the A group is bonded to therest of the compound of the formula (I) via the bond marked with *. 29.The electronic device according to claim 20, wherein the compound of theformula (I) corresponds to one of the following formulae:

where X, L¹, Ar¹ and k are as defined in claim 20, and where thecompounds may each be substituted on the benzene rings at the positionsshown as unsubstituted by R² radicals as defined in claim
 20. 30. Theelectronic device according to claim 20, wherein there is at least onefurther layer that does not include any compound of the formula (I)between the layer comprising the compound of the formula (I) and theemitting layer closest to the anode.
 31. The electronic device accordingto claim 30, wherein the at least one further layer is ahole-transporting layer comprising a monoamine compound containing atleast one group selected from spirobifluorenyl groups, phenanthrenylgroups, fluorenyl groups, carbazolyl groups, dibenzofuranyl groups anddibenzothiophenyl groups.
 32. The electronic device according to claim20, wherein the hole-transporting layer directly adjoins the anode, inthat there are at least two further layers arranged between thehole-transporting layer and the emitting layer, and in that there are nofurther emitting layers arranged between the emitting layer and theanode.
 33. A compound of a formula (S)

where an A group has to be bonded to at least one group selected fromthe B₁ and B₂ groups, and where the variables that occur are as follows:B₁, B₂ are the same or different at each instance and are N or CR² or C,where a B₁ or B₂ group is C in the specific case when an A group isbonded to it; Z is the same or different at each instance and is CR² orN or C, where a Z group is C in the specific case when an E group isbonded to the Z group in question; A is an arylamino group optionallysubstituted by one or more R¹ radicals, or a carbazole-containing groupoptionally substituted by one or more R¹ radicals; E is a single bond; Xis O or S; R¹ is the same or different at each instance and is selectedfrom H, D, F, C(═O)R³, CN, Si(R³)₃, N(R³)₂, P(═O)(R³)₂, OR³, S(═O)R³,S(═O)₂R³, straight-chain alkyl or alkoxy groups having 1 to 20 carbonatoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbonatoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromaticring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ringsystems having 5 to 40 aromatic ring atoms; where two or more R¹radicals may be joined to one another and may form a ring; where thealkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromaticring systems and heteroaromatic ring systems mentioned may each besubstituted by one or more R³ radicals; and where one or more CH₂ groupsin the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may bereplaced by —R³C═CR³—, —C≡C—, Si(R³)₂, C═O, C═NR³, —C(═O)O—, C(═O)NR³—,NR³, P(═O)(R³), —O—, —S—, SO or SO₂; R² is the same or different at eachinstance and is selected from H, D, F, C(═O)R³, CN, Si(R³)₃, N(R³)₂,P(═O)(R³)₂, OR³, S(═O)R³, S(═O)₂R³, straight-chain alkyl or alkoxygroups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxygroups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ringatoms, and heteroaromatic ring systems having 5 to 40 aromatic ringatoms; where two or more R² radicals may be joined to one another andmay form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groupsmentioned and the aromatic ring systems and heteroaromatic ring systemsmentioned may each be substituted by one or more R³ radicals; and whereone or more CH₂ groups in the alkyl, alkoxy, alkenyl and alkynyl groupsmentioned may be replaced by —R³C═CR³—, —C≡C—, Si(R³)₂, C═O, C═NR³,—C(═O)O—, C(═O)NR³—, NR³, P(═O)(R³), —O—, —S—, SO or SO₂; R³ is the sameor different at each instance and is selected from H, D, F, C(═O)R⁴, CN,Si(R⁴)₃, N(R⁴)₂, P(═O)(R⁴)₂, OR⁴, S(═O)R⁴, S(═O)₂R⁴, straight-chainalkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclicalkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynylgroups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40aromatic ring atoms, and heteroaromatic ring systems having 5 to 40aromatic ring atoms; where two or more R³ radicals may be joined to oneanother and may form a ring; where the alkyl, alkoxy, alkenyl andalkynyl groups mentioned and the aromatic ring systems andheteroaromatic ring systems mentioned may each be substituted by one ormore R⁴ radicals; and where one or more CH₂ groups in the alkyl, alkoxy,alkenyl and alkynyl groups mentioned may be replaced by —R⁴C═CR⁴—,—C≡C—, Si(R⁴)₂, C═O, C═NR⁴, —C(═O)O—, C(═O)NR⁴—, NR⁴, P(═O)(R⁴), —O—,—S—, SO or SO₂; R⁴ is the same or different at each instance and isselected from H, D, F, CN, alkyl or alkoxy groups having 1 to 20 carbonatoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromaticring systems having 6 to 40 aromatic ring atoms and heteroaromatic ringsystems having 5 to 40 aromatic ring atoms; where two or more R¹radicals may be joined to one another and may form a ring; and where thealkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems andheteroaromatic ring systems mentioned may be substituted by F or CN; iis 0 or
 1. 34. The compound according to claim 33, wherein X is O. 35.The compound according to claim 33, wherein i is
 1. 36. The compoundaccording to claim 33, wherein an A group is bonded to exactly one ofthe two B₁ and B₂ groups, and in that no A group is bonded to the otherof the two B₁ and B₂ groups.
 37. The compound according to claim 33,wherein the compound corresponds to a formula (S-1-1)

where the compounds may each be substituted on the benzene rings at thepositions shown as unsubstituted by R² radicals, and where the variablesthat occur as follows: L¹ is the same or different at each instance andis C═O, Si(R¹)₂, PR¹, P(═O)(R¹), O, S, SO, SO₂, an alkylene group having1 to 20 carbon atoms or an alkenylene or alkynylene group having 2 to 20carbon atoms, where one or more CH₂ groups in the groups mentioned maybe replaced by C═O, C═NR¹, C═O—O, C═O—NR¹, Si(R¹)₂, NR¹, P(═O)(R¹), O,S, SO or SO₂ and where one or more hydrogen atoms in the abovementionedgroups may be replaced by D, F or CN, or an aromatic or heteroaromaticring system which has 6 to 24 aromatic ring atoms and may be substitutedby one or more R¹ radicals; Ar¹ is the same or different at eachinstance and is an aromatic or heteroaromatic ring system which has 6 to30 aromatic ring atoms and may be substituted by one or more R¹radicals; k is 0, 1, 2 or 3; R¹, R², R³ and R⁴ are as defined in claim33.
 38. A process for preparing the compound according to claim 33,wherein it comprises an addition of a metallated ether or thioethercompound onto a diaryl ketone and a subsequent ring-closure reaction.